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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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 5-phenylpentyl iodide and hexamethylphosphoramide gives 3-(7-phenyl-1-heptynyl)-5-trimethylsilylfuran.
Sources & evidence
- ORD record
- ord-37cabc7bc2ca4ec581d6625176683b9a
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04957917
Reaction notes
Loading…