Aluminium lithium hydride → (1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrol-2-yl)methanol

HRID 1404183Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[C:9]2[C:17](OC)=[O:18])=[CH:4][CH:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:32]=[CH:31][C:30]([C:33]([F:39])([F:38])[C:34]([F:37])([F:36])[F:35])=[C:29]2[C:40](OC)=[O:41])=[CH:24][CH:23]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:15])[F:16])=[C:9]2[CH2:17][OH:18])=[CH:6][CH:7]=1.[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([N:28]2[CH:32]=[CH:31][C:30]([C:33]([F:38])([F:39])[C:34]([F:36])([F:37])[F:35])=[C:29]2[CH2:40][OH:41])=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Into a 25-mL round-bottom flask, was placed methyl 1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate and methyl 1-(4-chlorophenyl)-3-(perfluoroethyl)-1H-pyrrole-2-carboxylate (200 mg, 0.66 mmol, 1.00 equiv), LAH (50 mg, 1.32 mmol, 2.00 equiv) and tetrahydrofuran (5 mL). The resulting solution was stirred for 2 h at 0° C. in a water/ice bath. The reaction was then quenched by the addition of 3 mL of water. The resulting solution was extracted with ethyl acetate (5×10 mL) and the organic layers combined. The resulting residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:6) to yield [1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrol-2-yl]methanol and (1-(4-chlorophenyl)-3-(perfluoroethyl)-1H-pyrrol-2-yl)methanol as yellow oil.

Workup

customInto a 25-mL round-bottom flask, was placed
customThe reaction was then quenched by the addition of 3 mL of water
extractionThe resulting solution was extracted with ethyl acetate (5×10 mL)

Sources & evidence

ORD record: ord-9c39ea3d93aa416aa8727cdd228afc0a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912227B1

Reaction notes

Loading…