Hydrochloric Acid → (E)-methyl 4-(1-(4-fluorophenyl)cyclohexyl)but-3-enoate

HRID 1506297Notes

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2(/[CH:15]=[CH:16]/CC#N)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.O.[C:21]([O:24][CH2:25]C)(=[O:23])[CH3:22]>CO>[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2(/[CH:15]=[CH:16]/[CH2:22][C:21]([O:24][CH3:25])=[O:23])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

HCl gas was bubbled through a solution of (E)-4-(1-(4-fluorophenyl)cyclohexyl)but-3-enenitrile (Intermediate I-11B, 769 mg, 3.16 mmol) in anhydrous methanol (20 mL), and the mixture was stirred in a sealed tube at 60° C. for 1 hr. After cooling, about 10 mL of water was added and the mixture was stirred at room temperature overnight. The mixture was then added to ethyl acetate and washed with water, brine dried over sodium sulfate and concentrated under reduced pressure to give the (E)-methyl 4-(1-(4-fluorophenyl)cyclohexyl)but-3-enoate (560 mg, 2.03 mmol, 64.1% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.30 (2H, dd, J=9.02, 5.28 Hz), 6.99 (2H, t, J=8.80 Hz), 5.51-5.56 (1H, m), 5.35-5.45 (1H, m), 3.68 (3H, s), 3.05 (2H, dd, J=6.82, 1.10 Hz), 1.90-2.00 (2H, m), 1.79-1.88 (2H, m), 1.45-1.63 (6H, m).

Workup

temperatureAfter cooling
stirringthe mixture was stirred at room temperature overnight
washwashed with water, brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-1b21ae6cfe5947efaf9e9f790ca06e0e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216972B2

Reaction notes

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