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

HRID 345888Notes

Reaction equation

HRID 345888 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

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 156632515-(Trimethylsilyl)furan-3-carbaldehyde

Product 1

HCID 199915873-(2,2-Dibromoethenyl)-5-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Sources & evidence

ORD record
ord-73a837d51013460681712867d7ad1c05
Source dataset
uspto-grants-1991_10
Patent number
US05059611

Reaction notes

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