Tetrahydrofuran → (4,4-Difluorocyclohexyl)methanol

To a solution of 4,4-difluorocyclohexanecarboxylic acid ethyl ester (0.50 g, 2.6 mmol) cooled to 0° C. in diethyl ether (20 mL) was added dropwise 1.0 M lithium aluminum hydride in tetrahydrofuran (2.6 mL, 2.6 mmol). The reaction was stirred for 30 min. The reaction was carefully quenched with water (2.0 mL) followed by the addition of 1.0 N NaOH (2 mL). The reaction mixture was stirred for 10 min, filtered through a pad of celite and washed with diethyl ether (20 mL). The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and concentrated to give the title compound as a crude oil (465 mg) which was used without further purification.

1. customThe reaction was carefully quenched with water (2.0 mL)
2. additionfollowed by the addition of 1.0 N NaOH (2 mL)
3. stirringThe reaction mixture was stirred for 10 min
4. filtrationfiltered through a pad of celite
5. washwashed with diethyl ether (20 mL)
6. customThe organic layer was collected
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-d91549bf33cb4ac8a727428019e858cf

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691878B2