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

Reaction equation

[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]1[O:7][CH:6]=[C:5]([CH:8]=O)[CH:4]=1.[C:12](Br)(Br)([Br:14])[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:13][C:12]([Br:14])=[CH:8][C:5]1[CH:4]=[C:3]([Si:2]([CH3:11])([CH3:10])[CH3:1])[O:7][CH:6]=1

Participants

Procedure

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.