4-Fluorophenethyl Alcohol → 1-[2-(4-fluorophenyl)ethyl]-2-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

HRID 1514642Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:6]=1[C:7]#[N:8].[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21]O)=[CH:16][CH:15]=1.C(C=C1CCP(C)C1(C)C)#N>C1(C)C=CC=CC=1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][N:3]2[C:4]([C:9]([F:10])([F:12])[F:11])=[CH:5][C:6]([C:7]#[N:8])=[C:2]2[CH3:1])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A 266 mg portion of 2-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile was dissolved in 10 ml of toluene, and 0.382 ml of 2-(4-fluorophenyl)ethanol and 352 mg of cyanomethylenetrimethylphospholan were added, followed by stirring at 100° C. for 1.5 hours. The reaction liquid was concentrated under a reduced pressure, and the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-1:4) to obtain 451 mg of 1-[2-(4-fluorophenyl)ethyl]-2-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile as a white solid.

Workup

customThe reaction liquid
concentrationwas concentrated under a reduced pressure
customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-1:4)

Sources & evidence

ORD record: ord-e3155ce5c0ce425197359780e322346d
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222274B2

Reaction notes

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