Citric Acid → 2-Fluoro-5-methoxybenzeneethanol

To a mixed solution of 2-fluoro-5-methoxybenzaldehyde (0.8 ml) in tetrahydrofuran (4 ml) and dimethylsulfoxide (4 ml), 1.97 g of trimethylsulfonium iodide and 308 mg of sodium hydride were added under ice-cooling, and the reaction solution was stirred at room temperature for 2 hours. To the reaction solution was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50)) to afford a crude product as a colorless oil. To a solution of the crude product in tetrahydrofuran (2 ml), 200 mg of Sodium cyanoborohydride and 0.4 ml of trifluoroborane-diethylether complex were added under ice-cooling, and the reaction solution was stirred at room temperature for 2 hours. To the reaction solution was added 10% aqueous citric acid, and the mixture was extracted with chloroform and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-30/70)) to afford the title compound as a colorless oil.

1. temperaturecooling
2. extractionthe mixture was extracted with ethyl acetate
3. washThe combined organic layers were washed with a saturated saline solution
4. dry with materialdried over anhydrous sodium sulfate
5. distillationThe solvent was distilled off under reduced pressure
6. customthe residue obtained
7. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50))
8. customto afford a crude product as a colorless oil
9. temperaturecooling
10. stirringthe reaction solution was stirred at room temperature for 2 hours
11. extractionthe mixture was extracted with chloroform
12. dry with materialdried over anhydrous sodium sulfate
13. distillationThe solvent was distilled off under reduced pressure
14. customthe residue obtained
15. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-30/70))

ORDレコード

ord-2c52ffbcaaa44b10b3a796fc2c88f24a

出典データセット

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08367708B2