Sodium hydride → HCID 86596144, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (165 mg, 4.05 mmol) in dry dimethylformamide (10 mL) under an atmosphere of dry nitrogen was added 4-fluorothiophenol (430 μL, 4.05 mmol) dropwise and the reaction was stirred for 15 min. A solution of (3αR/S,5αS/R,6αR/S,6βR/S)-octahydro-1H-cyclopropa[3,4]benzo[1,2-c]furan-1-one (202 mg, 1.35 mmol) in dry dimethylformamide (2 mL) was added to the reaction mixture and was heated to 110° C. for 4.5 h. The reaction mixture was cooled to room temperature and quenched with aqueous 10% HCl, the product extracted with ethyl acetate, and dried on anhydrous sodium sulfate. The solvent was removed in vacuo and the product was purified by flash chromatography over silica gel (ethyl acetate/hexanes, 2/8+0.5% AcOH) to afford the desired product (1R/S,2R/S,3R/S,6S/R)-3-{[(4-fluorophenyl)-sulfanyl]methyl}bicyclo[4.1.0]heptane-2-carboxylic acid.

Provenance & Evidence