Water → 2-[Hydroxy(4-methoxyphenyl)methylidene]-5-(propan-2-yl)thiophen-3(2H)-one

HRID 1445335Notes

Reaction equation

C([O:8][C:9]1[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[S:11][C:10]=1[C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)=[O:18])C1C=CC=CC=1.O>ClCCl>[OH:8][C:9]1[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[S:11][C:10]=1[C:17]([C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1)=[O:18]

Participants

Conditions

Temperature: 22 °C

Procedure

1.00 g of (3-benzyloxy-5-isopropyl-thiophen-2-yl)-(4-methoxy-phenyl)-methanone was dissolved in 20 ml of dichloromethane. 2.73 ml of a 1 molar solution of boron tribromide-dimethyl sulfide complex in dichloromethane were added to the reaction solution. The solution was stirred at 22° C. for 1.5 h. The reaction mixture was poured into 50 ml of water, and the mixture was extracted twice with 30 ml of dichloromethane each time. The combined organic phase was extracted twice with 30 ml of saturated sodium bicarbonate solution each time and washed one with 50 ml of saturated sodium chloride solution, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (SiO2, ethyl acetate/n-heptane=1:4).

Workup

extractionthe mixture was extracted twice with 30 ml of dichloromethane each time
extractionThe combined organic phase was extracted twice with 30 ml of saturated sodium bicarbonate solution each time
washwashed one with 50 ml of saturated sodium chloride solution
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe crude product was purified by column chromatography (SiO2, ethyl acetate/n-heptane=1:4)

Sources & evidence

ORD record: ord-5077c04ea38e4105aa2ec02dd3f4fde4
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666848B2

Reaction notes

Loading…