Hydrochloric Acid → [4-({5-(2-phenylethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)phenyl]methanol

HRID 507924Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][C:9]2[NH:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[C:1]1([CH2:7][CH2:8][C:9]2[N:13]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[CH:28][CH:27]=3)[N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=3)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-(2-phenylethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazole (318 mg, 1.01 mmol), [4-(chloromethyl)phenyl]methanol (240 mg, 1.53 mmol), potassium carbonate (276 mg, 2.0 mmol) and N,N-dimethylformamide (10 mL) was stirred at 120° C. for 1 hr. The reaction mixture was poured into 1 N hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.) and concentrated. The residue was purified by silica gel column chromatography (10%-80% ethyl acetate/hexane) to give the title compound (220 mg, yield 50%) as a yellow oil.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe ethyl acetate layer was dried
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (10%-80% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-2eb1e7ce439641e18f08f3781a17bd56
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786165B2

Reaction notes

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