Tetrahydrofuran → HCID 58873068, compound

Participants

Reaction Conditions

Reaction Steps

Add a solution of the bromoethyl acetate (2.13 ml, 19.17 mmol) in THF (10 ml) dropwise to a −78 ° C. solution of the lithium hexamethylsillylamide (1M, 21 ml, 20.7 mmol) in THF. Stir the mixture at −78° C. for 10 minutes and treat with a dropwise solution of 2-(4-tert-butyl-benzoyl)-3,3-bis-methylsulfanyl-acrylonitrile (2.25 g, 7.67 mmol) in THF (20 ml). Stir the mixture at −78° C. for 30 minutes and at RT for 6 h. Pour into a saturated solution of ammonium chloride (100 ml). Extract organic with EtOAc (3×100 ml). Combine the organics wash with water (3×100 ml), brine (100 ml), dry over magnesium sulfate, filter and concentrate under reduced pressure. Purification by flash chromatography, eluting with ethyl acetate:hexanes (1:9) provides the title compound (1 g, 38%): Mass spectrum (M+1)=344.

Provenance & Evidence