Hydrochloric Acid → (4-(Cyclohexylmethyl)-3-(trifluoromethyl)phenyl)methanol

HRID 1964114Notes

Reaction equation

[CH:1]1([CH2:7][C:8]2[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[CH:10][C:9]=2[C:18]([F:21])([F:20])[F:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Li+].C1COCC1.Cl>O1CCOCC1.O>[CH:1]1([CH2:7][C:8]2[CH:17]=[CH:16][C:11]([CH2:12][OH:13])=[CH:10][C:9]=2[C:18]([F:19])([F:20])[F:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of methyl 4-(cyclohexylmethyl)-3-(trifluoromethyl)benzoate (280 mg, 0.93 mmol) in dioxane (8 mL) was added 2 M lithium borohydride in THF solution (0.93 mL, 1.86 mmol). The reaction mixture was heated at 80° C. for 2 h, cooled down, poured into water, acidified with 1 M HCl aqueous solution to pH 4, extracted with ethyl acetate. The combined organics were washed with saturated NaHCO3 solution and water, dried and concentrated. The residue was purified by silica gel column chromatography to give the title compound (190 mg) as colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 0.96-1.06 (m, 2H), 1.14-1.22 (m, 3H), 1.62-1.72 (m, 6H), 2.67 (d, J=6.7 Hz, 2H), 4.71 (d, J=5.7 Hz, 2H), 7.29 (d, J=7.9 Hz, 1H), 7.45 (dd, J=8.0 and 1.6 Hz, 1H), 7.62 (d, J=1.6 Hz, 1H).

Workup

temperaturecooled down
extractionextracted with ethyl acetate
washThe combined organics were washed with saturated NaHCO3 solution and water
customdried
concentrationconcentrated
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-0b1c7c6df2fd4347a1f54f120afd26e9
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415484B2

Reaction notes

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