Water → 3-{[2-(4,5-Diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}-2-methylphenol

HRID 1067134Notes

Reaction equation

C[O:2][C:3]1[C:4]([CH3:33])=[C:5]([CH:30]=[CH:31][CH:32]=1)[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH:9]=[C:8]1[C:13]1[O:14][C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1.B(Br)(Br)Br.O>C(Cl)Cl>[C:18]1([C:16]2[N:17]=[C:13]([C:8]3[CH:7]([CH2:6][C:5]4[C:4]([CH3:33])=[C:3]([OH:2])[CH:32]=[CH:31][CH:30]=4)[CH2:12][CH2:11][CH2:10][CH:9]=3)[O:14][C:15]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 2-[1-(3-methoxy-2-methylbenzyl)-2-cyclohexen-2-yl]-4,5-diphenyloxazole (1.16 g) in CH2Cl2 (25 ml) was added boron tribromide (1M solution in CH2Cl2, 5.32 ml) at −60° C. and the mixture was warmed to 5° C. After stirring for 1 hour at the same temperature, the reaction mixture was stirred for further 1 hour at room temperature. To the mixture was added water under ice-cooling, extracted with EtOAc. The organic layer was washed with water, saturated sodium hydrogen carbonate, water, and brine, dried over magnesium sulfate, evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 5:1) to give 3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}-2-methylphenol (903.8 mg) as an amorphous solid.

Workup

stirringthe reaction mixture was stirred for further 1 hour at room temperature
temperaturecooling
extractionextracted with EtOAc
washThe organic layer was washed with water, saturated sodium hydrogen carbonate, water, and brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified by silica gel column chromatography (hexane-EtOAc 5:1)

Sources & evidence

ORD record: ord-dccc98888f3d4257b7b2609004fae252
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06245790B1

Reaction notes

Loading…