Sodium hydride → 1-{1-[4-(Propan-2-yl)phenyl]cyclopropyl}ethan-1-one

HRID 1359552Notes

Reaction equation

[H-].[Na+].[I-].[CH3:4][S+](C)C.[CH3:8][CH:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17](=[CH2:21])[C:18](=[O:20])[CH3:19])=[CH:13][CH:12]=1)[CH3:10]>CN(C)C=O>[CH3:10][CH:9]([C:11]1[CH:12]=[CH:13][C:14]([C:17]2([C:18](=[O:20])[CH3:19])[CH2:4][CH2:21]2)=[CH:15][CH:16]=1)[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

474 mg of sodium hydride (55% in paraffin oil) is introduced into 20 ml of dimethylformamide under nitrogen at 0° C., and 1.29 g of trimethylsulfonium iodide is added. After 30 minutes at this temperature, 930 mg of ketone 46 is added in drops to 4 ml of dimethylformamide. It is stirred for 1 more hour at 0° C., then quenched with sodium chloride solution, extracted with ethyl acetate, dried on sodium sulfate and concentrated by evaporation. After chromatography on silica gel with ethyl acetate/hexane, 447 mg of title compound 47 is obtained as a colorless oil.

Workup

customquenched with sodium chloride solution
extractionextracted with ethyl acetate
customdried on sodium sulfate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-eacb9d4568c64530943976a6ec5ff0eb
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06600058B1

Reaction notes

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