tert-Butyl methyl ether → HCID 76621206, compound

Participants

Reaction Steps

500 mg (1.01 mmol) of (2), 38 mg (0.203 mmol) of CuI and 71 mg (0.1 eq.) of PdCl2(PPh)3 were dissolved in 10 ml of Et3N. to The solution was flushed with Argon and 1.68 ml (1.216 mmol) of ethynyl-trimethyl silane were added and stirred for 2 h at room temperature. The reaction mixture was poured into MTBE, washed with saturated NaHCO3, brine and dried over Na2SO4. The solvent was removed at the evaporator. The crude product was dissolved in 20 ml of THF and cooled to −78° C. 2 ml (2 mmol) of 1 M TBAF solution in THF were added and the reaction mixture was stirred for 45 min at −78° C. 10 ml of water were added and the product was extracted with diethyl ether. The organic layer was extracted with saturated NaHCO3, brine and dried over Na2SO4. The solvent was removed at the evaporator. The product was purified by column chromatography on silica gel using ethyl acetate/hexane to give 195 mg of (3).

Provenance & Evidence