Hexane → HCID 18431832, compound

Participants

Reaction Conditions

Reaction Steps

In a round bottom flask equipped with a magnetic stirbar is placed 1,2-bis(trimethylsilyloxy)ethane (1.3 eq.) in CH2Cl2 containing trimethysilyltrifluoromethanesulfonate at -78° C. To this is added, within 20 minutes, a solution of 1 (1 eq) in CH2Cl2. The reaction is stirred for 1 hour at -78° C. and then slowly warmed to 25° C. for 1 hour. The reaction is quenched at 0° C. with water, extracted with CH2Cl2 (3 times), dried (MgSO4), and concentrated in vacuo to give crude 2. To a well stirred solution of crude 2 (1 eq) in methanol at 0° C. is added a suspension of sodium methoxide (1.2 eq) in MeOH. The reaction is stirred at 0° C. for 1 hour and then warmed to 25° C. for 1 hour. The reaction is neutralized with acidic ion exchange resin which is washed thoroughly with MeOH (5×). The filtrate is concentrated in vacuo to give a syrup which is subjected to flash chromatography on silica gel eluting with 4:1 hexane:ethyl acetate and 2% MeOH in CH2Cl2 to give 3.

Provenance & Evidence