(Triphenylphosphoranylidene)acetaldehyde → (E)-3-(5-Chlorobenzofuran-2-yl)-prop-2-enal

HRID 377370Notes

Reaction equation

HRID 377370 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]=O)=[CH:7][C:6]=2[CH:12]=1.[CH:13]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:14].CCCCCCC.CCOC(C)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](/[CH:10]=[CH:15]/[CH:13]=[O:14])=[CH:7][C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 134001705-Chloro-1-benzofuran-2-carbaldehydeHCID 21899848Ethylacetate heptane

Product 1

HCID 19358687(E)-3-(5-Chlorobenzofuran-2-yl)-prop-2-enalYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-chlorobenzofuran-2-carboxaldehyde (813 mg, 4.50 mmol) and formylmethylene triphenylphosphorane (1.37 g, 4.50 mmol) in CH2Cl2 (40 ml) was treated as sen in preparation 1. After a chromatography on silicagel (n-heptane/EtOAc 4/1) pure title compound (640 mg, 3.10 mmol, yield 68.8%) as yellow crystals was obtained.

Workup

  1. customas sen in preparation 1

Sources & evidence

ORD record
ord-1105720e67994fec882afba7b638ffd7
Source dataset
uspto-grants-2000_02
Patent number
US06025390

Reaction notes

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