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With sodium hydroxide In tetrahydrofuran; methanol; chloroform; water; ethyl acetate
C. 5-(Hydroxymethyl)thiazole To a precooled (ice bath) three neck 500 mL flask containing lithium aluminum hydride (2.89 g, 76 mmol) in 250 mL of THF was added ethyl thiazole-5-carboxylate (11.82 g, 75.68 mmol) in 100 mL of THF dropwise over 1.5 hours to avoid excess foaming. The reaction was stirred for an additional hour, and treated cautiously with 2.9 mL of water, 2.9 mL of 15percent NaOH, and 8.7 mL of water. The solid salts were filtered, and the filtrate set aside. The crude salts were heated at reflux in 100 mL of ethyl acetate for 30 minutes. The resulting mixture was filtered, and the two filtrates were combined, dried over Na2 SO4, and concentrated in vacuo. The product was purified by silica gel chromatography eluding sequentially with 0percent -2percent -4percent methanol in chloroform, to provide the desired compound, Rf-0.3 (4percent methanol in chloroform), which solidified upon standing in 75percent yield. NMR (CDCl3) δ4.92 (s, 2H), 7.78 (s, 1H), 8.77 (s, 1H). Mass spectrum: (M+H)+ =116.
75%
With sodium hydroxide In tetrahydrofuran; methanol; chloroform; water; ethyl acetate
P. 5-(Hydroxymethyl)thiazole To a precooled (ice bath) three neck 500 mL flask containing lithium aluminum hydride (76 mmol) in 250 mL of THF was added ethyl thiazole-5-carboxylate (11.82 g, 75.68 mmol) in 100 mL of THF dropwise over 1.5 hours to avoid excess foaming. The reaction was stirred for an additional hour, and treated cautiously with 2.9 mL of water, 2.9 mL of 15percent NaOH, and 8.7 mL of water. The solid salts were filtered, and the flitrate set aside. The crude salts were heated at reflux in 100 mL of ethyl acetate for 30 min. The resulting mixture was filtered, and the two filtrates were combined, dried over Na2 SO4, and concentrated in vacuo. The product was purified by silica gel chromatography eluding sequentially with 0percent -2percent-4percent methanol in chloroform, to provide the desired compound, Rf=0.3 (4percent methanol in chloroform), which solidified upon standing in 75percent yield. NMR (CDCl3)δ4.92 (s, 2H), 7.78 (s, 1H), 8.77 (s, 1H). Mass spectrum: (M+H)+ =116.
75%
With sodium hydroxide In tetrahydrofuran; methanol; chloroform; water; ethyl acetate
K. 5-(Hydroxymethyl)thiazole To a precooled (ice bath) three neck 500 mL flask containing lithium aluminum hydride (76 mmol) in 250 mL of THF was added ethyl thiazole-5-carboxylate (11.82 g, 75.68 mmol) in 100 mL of THF dropwise over 1.5 hours to avoid excess foaming. The reaction was stirred for an additional hour, and treated cautiously with 2.9 mL of water, 2.9 mL of 15percent NaOH, and 8.7 mL of water. The solid salts were filtered, and the filtrate set aside. The crude salts were heated at reflux in 100 mL of ethyl acetate for 30 min. The resulting mixture was filtered, and the two filtrates were combined, dried over Na2 SO4, and concentrated in vacuo. The product was purified by silica gel chromatography eluding sequentially with 0percent - 2percent - 4percent methanol in chloroform, to provide the desired compound, Rf=0.3 (4percent methanol in chloroform), which solidified upon standing in 75percent yield. NMR (CDCl3) δ4.92 (s, 2H), 7.78 (s, 1 H), 8.77 (s, 1H). Mass spectrum: (M+H)+ =116.
75%
With sodium hydroxide In tetrahydrofuran; methanol; chloroform; water; ethyl acetate
K. 5-(Hydroxymethyl)thiazole. To a precooled (ice bath) three neck 500 mL flask containing lithium aluminum hydride (76 mmol) in 250 mL of THF was added ethyl thiazole-5-carboxylate (11.82 g, 75.68 mmol) in 100 mL of THF dropwise over 1.5 hours to avoid excess foaming. The reaction was stirred for an additional hour, and treated cautiously with 2.9 mL of water, 2.9 mL of 15percent NaOH, and 8.7 mL of water. The solid salts were filtered, and the filtrate set aside. The crude salts were heated at reflux in 100 mL of ethyl acetate for 30 min. The resulting mixture was filtered, and the two filtrates were combined, dried over Na2 SO4, and concentrated in vacuo. The product was purified by silica gel chromatography eluding sequentially with 0percent-2percent-4percent methanol in chloroform, to provide the desired compound, Rf=0.3 (4percent methanol in chloroform), which solidified upon standing in 75percent yield. NMR (CDCl3) δ4.92 (s, 2H), 7.78 (s, 1H), 8.77 (s, 1H). Mass spectrum: (M+H)+ =116.
75%
With sodium hydroxide In tetrahydrofuran; methanol; chloroform; water; ethyl acetate
D. 5-(Hydroxymethyl)thiazole To a precooled (ice bath) three neck 500 mL flask containing lithium aluminum hydride (76 mmol) in 250 mL of THF was added ethyl thiazole-5-carboxylate (11.82 g, 75.68 mmol)in 100 mL of THF dropwise over 1.5 hours to avoid excess foaming. The reaction was stirred for an additional hour, and treated cautiously with 2.9 mL of water, 2.9 mL of 15percent NaOH, and 8.7 mL of water. The solid salts were filtered, and the filtrate set aside. The crude salts were heated at reflux in 100 mL of ethyl acetate for 30 min. The resulting mixture was filtered, and the two flitrates were combined, dried over Na2 SO4, and concentrated in vacuo. The product was purified by silica gel chromatography eluding sequentially with 0percent-2percent-4percent methanol in chloroform, to provide the desired compound, Rf=0.3 (4percent methanol in chloroform), which solidified upon standing in 75percent yield. NMR (CDCl3) δ4.92 (s, 2 H), 7.78 (s, 1 H), 8.77 (s, 1 H). Mass spectrum: (M+H)+ =116.
Reference：
[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 7, p. 3124 - 3153
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 4, p. 602 - 617
[3] Patent: US5914332, 1999, A,
[4] Patent: US5455351, 1995, A,
[5] Patent: US5559158, 1996, A,
[6] Patent: US5484801, 1996, A,
[7] Patent: US5461067, 1995, A,
[8] Patent: EP1170289, 2002, A2, . Location in patent: Page 44-45
[9] Helvetica Chimica Acta, 1952, vol. 35, p. 215
[10] Journal of Medicinal Chemistry, 1973, vol. 16, p. 978 - 984
[11] Patent: US5559158, 1996, A,
[12] Patent: US5484801, 1996, A,
B. Ethyl Thiazole-5-carboxylate To a round bottom flask was added 250 mL of dry acetone, 7.5 g (0.123 mol) of thioformamide, and 18.54 g (0.123 mol) of <strong>[33142-21-1]ethyl 2-chloro-2-formylacetate</strong>. The reaction was heated at reflux for 2 hours. The solvent was removed in vacuo, and the residue was purified by chromatography (SiO2, 6 cm o.d. column, 100% CHCl3, Rf =0.25) to provide 11.6 g (60%) of the desired compound as a light yellow oil. NMR (CDCl3 delta1.39 (t, J=7 Hz, 3H), 4.38 (q, J=7 Hz, 2H), 8.50 (s, 1H), 8.95 (s, 1H).
11.6 g (60%)
In chloroform; acetone;
O. Ethyl Thiazole-5-carboxylate To a round bottom flask was added 250 mL of dry acetone, 7.5 g (0.123 mol) of thioformamide, and 18.54 g (0.123 mol) of <strong>[33142-21-1]ethyl 2-chloro-2-formylacetate</strong>. The reaction was heated at reflux for 2 hours. The solvent was removed in vacuo, and the residue was purified by chromatography (SiO2, 6 cm o.d. column, 100% CHCl3, Rf =0.25) to provide 11.6 g (60%) of the desired compound as a light yellow oil. NMR (CDCl3)delta1.39 (t, J=7 Hz, 3H), 4.38 (q, J=7 Hz, 2H), 8.50 (s, 1H), 8.95 (s, 1H).
11.6 g (60%)
In chloroform; acetone;
J. Ethyl Thiazole-5-carboxylate To a round bottom flask was added 250 mL of dry acetone, 7.5 g (0.123 mol) of thioformamide, and 18.54 g (0.123 mol) of <strong>[33142-21-1]ethyl 2-chloro-2-formylacetate</strong>. The reaction was heated at reflux for 2 hours. The solvent was removed in vacuo, and the residue was purified by chromatography (SiO2, 6 cm o.d. column, 100% CHCl3, Rf =0.25) to provide 11.6 g (60%) of the desired compound as a light yellow oil. NMR (CDCl3) delta1.39 (t, J=7 Hz, 3H), 4.38 (q, J=7 Hz, 2H), 8.50 (s, 1H), 8.95 (s, 1H).
11.6 g (60%)
In chloroform; acetone;
J. Ethyl Thiazole-5-carboxylate. To a round bottom flask was added 250 mL of dry acetone, 7.5 g (0.123 mol) of thioformamide, and 18.54 g (0.123 mol) of ethyl 2-chloro-2 -formylacetate. The reaction was heated at reflux for 2 hours. The solvent was removed in vacuo, and the residue was purified by chromatography (SiO2, 6 cm o.d. column, 100% CHCl3, Rf=0.25) to provide 11.6 g (60%) of the desired compound as a light yellow oil. NMR (CDCl3) delta1.39 (t, J=7 Hz, 3H), 4.38 (q, J=7 Hz, 2H), 8.50 (s, 1H), 8.95 (s, 1H).
11.6 g (60%)
In chloroform; acetone;
C. Ethyl Thiazole-5-carboxylate To a round bottom flask was added 250 mL of dry acetone, 7.5 g (0.123 mol) of thioformamide, and 18.54 g (0.123 mol) of <strong>[33142-21-1]ethyl 2-chloro-2-formylacetate</strong>. The reaction was heated at reflux for 2 hours. The solvent was removed in vacuo, and the residue was purified by chromatography (SiO2, 6 cm o.d. column, 100% CHCl3, Rf =0.25) to provide 11.6 g (60%) of the desired compound as a light yellow oil. NMR (CDCl3) delta1.39 (t, J=7 Hz, 3 H), 4.38 (q, J=7 Hz, 2 H), 8.50 (s, 1 H), 8.95 (s, 1 H).
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