Water → (2-Cyclopropyl-6-fluorophenyl)-methanol

Temperature

0 °C

To a solution of methyl 2-cyclopropyl-6-fluorobenzoate (3, 4.54 g, 23.4 mmol) in anhydrous tetrahydrofuran (30 mL) at room temperature was added lithium aluminium hydride (1.42 g, 37.4 mmol) in small portions and the mixture was stirred overnight. The reaction mixture was cooled to 0° C. and water (3 mL) was added dropwise, the mixture was warmed to room temperature and an additional portion of water (30 mL) was added. The solids were removed by filtration, and the aqueous filtrate was extracted with ethyl acetate (2×30 mL). The combined organic layers were dried over magnesium sulfate and evaporated. Purification by column chromatography over silica using n-hexane:ethyl acetate (8:1) as eluent afforded the title compound (3.28 g, 19.8 mmol, 84%) as a pale yellow oil.

1. temperaturethe mixture was warmed to room temperature
2. customThe solids were removed by filtration
3. extractionthe aqueous filtrate was extracted with ethyl acetate (2×30 mL)
4. dry with materialThe combined organic layers were dried over magnesium sulfate
5. customevaporated
6. customPurification by column chromatography over silica

ORD record

ord-e3cc394d2a884e95954ff5261daf5294

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680099B2