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CAS No. : | 63485-50-7 | MDL No. : | MFCD18483124 |
Formula : | C6H10O3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | BYKHAEUVLSBWSU-UHFFFAOYSA-N |
M.W : | 130.14 | Pubchem ID : | 12815112 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 72h; | Triphenylphosphine (6.14 g, 23.4 mmol) was added to a solution of 2-methoxy-5- fluorophenol (2.25 g, 15.6 mmol) in tetrahydrofuran (40 mL). The reaction mixture was cooled to 0 C, and (c/s)-methyl 3-hydroxycyclobutanecarboxylate (2.44 g, 18.7 mmol) was added, followed by DIAD (4.6 mL, 23 mmol). The reaction mixture was then warmed to room temperature, stirred for 3 days, and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc. The organics were washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 30%-70% EtOAc-hexanes gradient to give the title compound as a colorless, thick oil (3.6 g, 91 %). 1H NMR (400 MHz, CD3SOCD3) delta 2.52-2.64 (m, 2 H), 2.74-2.83 (m, 2 H), 3.15- 3.27 (m, 1 H), 3.76 (s, 3 H), 3.86 (s, 3 H), 4.90 (t, J = 7 Hz, 1 H), 6.48 (dd, J = 10, 3 Hz, 1 H), 6.62 (td, J = 8, 3 Hz, 1 H), 6.81 (dd, J = 9, 5 Hz, 1 H); LC-MS (LC-ES) peak at T = 0.78 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 72h; | Triphenylphosphine (1 .21 g, 4.60 mmol) was added to a solution of 5-fluoroquinolin-8- ol (500 mg, 3.06 mmol) in tetrahydrofuran (10 mL). The reaction mixture was cooled to 0 C, and methyl 3-hydroxycyclobutanecarboxylate (0.49 mL, 4.6 mmol) was added, followed by DIAD (0.89 mL, 4.6 mmol). After 10 min, the reaction mixture was warmed to room temperature, stirred for 3 days and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc (2X). The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 0%-100% EtOAc-hexanes gradient to give a mixture of cis and trans isomers which were separated on a Whelk O RR 20 X 250 mm column eluting with 40% EtOH in hexanes to give the title compound (415 mg, 49%). 1H NMR (400 MHz, CD3SOCD3) delta 2.48-2.55 (m, 2 H), 2.77 (ddd, J = 13, 7, 4 Hz, 2 H), 3.21 -3.29 (m, 1 H), 3.66 (s, 3 H), 5.04 (t, J = 7 Hz, 1 H), 6.96 (dd, J = 9, 5 Hz, 1 H), 7.32 (dd, J = 10, 9 Hz, 1 H), 7.68 (dd, J = 8, 4 Hz, 1 H), 8.44 (dd, J = 8, 2 Hz, 1 H), 8.97 (dd, J = 4, 2 Hz, 1 H); LC-MS (LC-ES) M+H = 276. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 72.0h; | 8-0I (Intermediate 126A) (380 mg, 2.23 mmol) in tetrahydrofuran (10 mL). The reaction mixture was cooled to 0 C, and methyl 3-hydroxycyclobutanecarboxylate (0.37 mL, 3.5 mmol) was added, followed by DIAD (0.68 mL, 3.5 mmol). After 10 min, the reaction mixture was warmed to room temperature, stirred for 3 days and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc (2X). The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 0%-1 00% EtOAc-hexanes gradient to give a mixture of cis and trans isomers which were separated on an IC 30 X 250 mm column eluting with 50% EtOH in hexanes to give the title compound (137 mg, 21 %). 1H NMR (400 MHz, CD3SOCD3) delta 2.48- 2.59 (m, 2 H), 2.82 (ddd, J = 14, 7, 5 Hz, 2 H), 3.22-3.32 (m, 1 H), 3.31 (s, 3 H), 5.07 (t, J = 7 Hz, 1 H), 6.91 (dd, J = 1 1 , 3 Hz, 1 H), 7.31 (dd, J = 9, 3 Hz, 1 H), 7.59 (dd, J = 8, 4 Hz, 1 H), 8.30 (dd, J = 8, 2 Hz, 1 H), 8.83 (dd, J = 4, 2 Hz, 1 H); LC-MS (LC-ES) M+H = 276. |
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