* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With water; potassium hydroxide In methanol for 2 h; Reflux
To a solution of compound 12 (1.40 g, 7.7 mmol) in MeOH (30 mL) was added an excess of KOH and the mixture was refluxed 2 h. The solvent was removed in vacuo, and the residue was partitioned between CH2Cl2 (20 mL) and H2O (20 mL). The separated organic phase was dried (Na2SO4) and concentrated in vacuo to give compound 13 as a pale yellow oil (1.00 g, 93percent yield). 1H NMR (CDCl3): δ 1.82 (s, 1H), 3.87 (s, 3H), 4.70 (s, 2H), 7.18-7.24 (m, 2H), 8.25 (1H, J = 2.8 Hz); GC/MS m/z 140 (M++1, 3) 139 (M+, 44), 138 (100), 110 (71).
56%
at 105℃; for 1.33333 h;
4) (5-Methoxy-pyridin-2-yl)-methanol Acetic acid 5-methoxy-pyridin-2-ylmethyl ester (10.5 g, 58 mmol) was dissolved in HCl (25percent, 30 ml) and the resultant reaction mixture was stirred at ca. 105° C. for 80 min under an argon atmosphere. Solid NaHCO3 was added in portions followed by aqueous K2CO3 solution to achieve an alkaline pH 10. This resultant mixture was extracted with ethyl acetate (4*) and the combined organic extracts were washed with water, brine, dried (MgSO4) filtered and then concentrated under reduced pressure. The crude oil was purified over silica gel (ethyl acetate/n-heptane 1:1 to 2:1): yellow solid 4.8 g (56percent); 1H NMR δ (CDCl3) δ 3.8 (br, 1H), 3.86 (s, 3H), 7.21 (m, 2H), 8.24 (m, 1H); MS: m/e=138.0 (M), 110.0 (M-CO).
Reference：
[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3913 - 3924
[2] Patent: US6194437, 2001, B1,
[3] Patent: US2006/14945, 2006, A1, . Location in patent: Page/Page column 40
[4] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 438 - 450
[5] Patent: WO2007/120729, 2007, A2, . Location in patent: Page/Page column 40
2
[ 29681-39-8 ]
[ 127978-70-5 ]
Yield
Reaction Conditions
Operation in experiment
78%
With diisobutylaluminium hydride In toluene at -78 - 0℃; Inert atmosphere
5-methoxypyridine-2-carboxylic acid methyl ester 8 (6.2 g, 37.1 mmol) was dissolved in toluene (370 ml) under a nitrogen atmosphere and cooled to -78°C. 1.0 M diisobutylaluminum hydride in toluene (130 ml, 130.0 mmol) was added through a syringe and the mixture was stirred at 0°C for 90 minutes. The mixture was then quenched with 300 ml of saturated aqueous potassium sodium tartrate and warmed to 25 °C for 1 hour. The reaction mixture was extracted three times with ethyl acetate. The organic extracts were combined, washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using 0-10percent methanol in ethyl acetate to give the title compound as a pale yellow solid (4.0 g, 78percent). 1H NMR (CD3COCD3) δ: 8.19 (d, J = 2.93 Hz, 1H), 7.43 (d, J = 8.61 Hz, 1H), 7.34 (dd, J = 8.61, 2.93 Hz, 1H), 4.66 (s, 2H), 3.85 (s, 3H).
With sodium tetrahydroborate In methanol at 0℃; for 0.166667 h;
To a mixture of 5-methoxypicolinaldehyde (326mgs, 2.36mmol) in MeOH (10 mL) was added NaBH4 (71.9 mg, 1.90 mmol) at O0C. The mixture was stirred at O0C for 10 min after concentration in vacuo, the residue was purified with ISCO MPLC (40-80percent EtOAc/hexane) to yield the title compound as a colorless oil (298 mg, 90 percent). 1H NMR (CDCl3) 68.28 (d, 1 H), 7.09 - 7.27 (m, 2 H), 4.73 (s, 2 H), 3.89 (s, 3 H). MS (M+H+) = 140.
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