Ethyl Acetate → HCID 11181172, compound

Participants

Reaction Steps

A solution of 17β-ethynyl-3α-(t-butyidiphenylsilyloxy)-5α-androstane (120 mg, 0.23 mmol) in pyrrolidine (2 mL) was added to a mixture of tetrakis triphenylposphine palladium (0) (13.28 mg, 0.0115 mmol) and CuI (4.4 mg, 0.023 mmol) in pyrrolidine (1 mL). To the resulting mixture was added 4-iodotoluene (150 mg, 0.69 mmol) and was stirred at RT for 24 h. Addition of saturated aqueous NH4Cl solution followed by ethyl acetate. Extraction of the organic layer with water and brine and drying (Na2SO4) followed by evaporation of the solvent in vacuo and subsequent purification of the residue with flash column chromatography using petroleum ether/acetone 80/20 as eluent afforded the desired compound named above.

Provenance & Evidence