Ethyl-4,4-difluorocyclohexane carboxylate → (4,4-Difluorocyclohexyl)methanol

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Reaction Conditions

Reaction Steps

Ethyl 4,4-difluorocyclohexanecarboxylate (10 g, 52.03 mmol) was dissolved in THF (100 mL) and cooled to 1° C. under nitrogen atmosphere. LAH (57.2 mL, 57.23 mmol) was added dropwise to the solution at a rate to keep the temperature below 10° C. The resulting mixture was allowed to reach 20° C. and stirred at that temperature for approximately 1 h. The reaction mixture was then cooled to 10° C. and quenched carefully by the sequential slow addition of 2.2 mL of water, 2.2 mL of 15 w/v % aqueous NaOH and 6.6 mL of water and stirred for 30 minutes at 20° C. The solids were removed by filtration and washed with THF. The reaction solution was dried over MgSO4 and evaporated in vacuo to give crude (4,4-difluoro-cyclohexyl)methanol (7.22 g, 92%). 1H NMR (400 MHz, cdcl3) δ 1.21-1.38 (m, 2H), 1.44 (s, 1H), 1.51-1.90 (m, 5H), 2.04-2.18 (m, 2H), 3.52 (d, 2H).

Provenance & Evidence