Carbon tetrabromide → 3-(2,2-Dibromoethenyl)-5-trimethylsilylfuran

Participants

Reaction Steps

5-Trimethylsilyl-3-furaldehyde is treated with carbon tetrabromide and triphenylphosphine in dichloromethane at 0° to give 3-(2,2-dibromoethenyl)-5-trimethylsilylfuran. Treating with n-butyl lithium and a protected iodoalcohol I(CH2)8 --OSI(CH3)2 t-Bu, which is 8-iodo-0-t-butyldimethylsilyloctan-1-ol, and hexamethylphosphoramide gives 3-[t-Bu(CH3)2SiO--(CH2)8C≡C]-5-trimethylsilylfuran which is hydrogenated and treated with acetic acid to give 3-(10-hydroxydecyl)-5-trimethylsilylfuran.

Provenance & Evidence