[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]1[O:4][CH:5]=[C:6]([CH:8]=O)[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:31](Br)(Br)([Br:33])[Br:32]>ClCCl>[Br:32][C:31]([Br:33])=[CH:8][C:6]1[CH:7]=[C:3]([Si:2]([CH3:11])([CH3:10])[CH3:1])[O:4][CH:5]=1A solution of 2-trimethylsilyl-4-furaldehyde (Compound 4, 1.0 g, 5.95 mmol) in dichloromethane (2 ml) was added to a solution of triphenylphosphine (3.9 g, 14.9 mmol) and carbon tetrabromide 2.46 g, 7.44 mmol) in dichloromethane (15 ml) at 0° under argon. After 1 hour, the mixture was extracted thoroughly with pentane. Evaporation of the pentane extracts gave an oil, which was flash chromatographed on silica using hexane. Fractions with Rf of about 0.52 on evaporation gave the title silylfuran as a yellow oil.
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