Methyl chloroformate → HCID 67604256, compound

Participants

Reaction Steps

2.3 ml of 1.5M pentene solution of t-butyllithum was dropwise added, at -78° C., to a solution 416 mg of (E)-3,4-dimethyl-1-iodo-1-pentene dissolved in 5 ml of diethyl ether. The reaction mixture was stirred at room temperature for 2 hours. Thereto was dropwise added a solution of 682 mg of 1-acetyl-4-(2-(3-(t-butyldimethylsilyloxy)-2-methylenebicyclo[3.1.0]hexane-1-yl)-2-methoxyethylidene)-2,3,3a,4,5,6,7,7a-octahydro-7a-methylindene dissolved in 10 ml of tetrahydrofuran. The mixture was stirred for 1 hour. Thereto was dropwise added 0.3 ml of methyl chloroformate. The mixture was stirred at room temperature overnight. The reaction mixture was mixed with an aqueous sodium hydrogencarbonate solution, followed by extraction with ethyl acetate. The extract was washed with an aqueous sodium hydrogencarbonate solution and concentrated under reduced pressure to obtain 1.04 g (2S,3E)-5,6-dimethyl-2-(4-(2-(3-(t-butyldimethylsilyloxy)-2-methylenebicyclo[3.1.0]hexane-1-yl)-2-methoxyethylidene)-2,3,3a,4,5,6,7,7a-octahydro-7a-methylinden-1-yl)-2-methoxycarbonyloxy-3-heptene having the follow property.

Provenance & Evidence