Phosphine → 1-(4-hydroxymethyl-phenyl)-ethanone O-(2-trifluoromethyl-biphenyl-4-ylmethyl)-oxime

HRID 547269Notes

Reaction equation

Cl[C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][N:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][CH:12]=2)[CH3:10])=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.P.[F-].[K+]>C1COCC1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:22][C:21]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([CH2:6][O:7][N:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][CH:12]=2)[CH3:10])[CH:19]=[CH:20][C:2]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(4-hydroxymethyl-phenyl)-ethanone O-(4-chloro-3-trifluoromethyl-benzyl)-oxime (1 eq), phenyl boronic acid (1.5 eq), Pd(OAc)2 (0.03 eq), phosphine ligand (0.06 eq) and KF (3 eq) in dry THF is heated at 100° C. in microwave for 30 minutes. The resulting mixture is diluted with EtOAc and washed with brine. The organic layer is dried over Na2SO4. After concentration, the residue is purified by column chromatography (30% EtOAc in hexane) to give 1-(4-hydroxymethyl-phenyl)-ethanone O-(2-trifluoromethyl-biphenyl-4-ylmethyl)-oxime as a white solid [MS: (ES+) 400.1 (M+1)+].

Workup

washwashed with brine
dry with materialThe organic layer is dried over Na2SO4
concentrationAfter concentration
customthe residue is purified by column chromatography (30% EtOAc in hexane)

Sources & evidence

ORD record: ord-34089bf7866b4f23bb1a9fec470858eb
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07939519B2

Reaction notes

Loading…