Hydrochloric Acid → 6-[(1E)-(3RS)-3-tert-butyldiphenylsilyloxy-1-undecenyl]-pyridine-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

1.16 ml of n-butyllithium (1.6 molar in hexane) is instilled in a suspension of 500 mg of 2-bromo-6-[(1E)-(3RS)-3-tert-butyldiphenylsilyloxy-1-undecenyl]-pyridine in 2 ml of diethyl ether and 1 ml of tetrahydrofuran at -80° C. under argon atmosphere. After completion of the addition, the reaction mixture is stirred for 15 minutes at -40° C., cooled to -80° C. and mixed by instillation at this temperature with 140 mg of dimethylformamide. After 4 hours at -80° C., the reaction mixture is hydrolyzed with 3 ml of 2 n hydrochloric acid, the organic phase is separated, dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/0-10% ethyl acetate. 385 mg of 6-[(1E)-(3RS)-3-tert- butyldiphenylsilyloxy-1-undecenyl]-pyridine-2-carbaldehyde is obtained as yellow oil.

Provenance & Evidence