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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1359552Generated: October 27, 2026

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

https://huagongshe.com/reaction/1359552

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
ReactantTrimethylsulfonium iodideHCID 75127—
Reactant3-[4-(1-Methylethyl)phenyl]-3-buten-2-oneHCID 18000858—
SolventDimethylformamideHCID 6228—
Product1-{1-[4-(Propan-2-yl)phenyl]cyclopropyl}ethan-1-oneHCID 1800091944.7%

Reaction Conditions

Temperature0 °C

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06600058B1
Source datasetuspto-grants-2003_07
ORD IDord-eacb9d4568c64530943976a6ec5ff0eb
Source noteuspto-grants-2003_07