(Triphenylphosphoranylidene)acetaldehyde → HCID 19358673, compound

HRID 377374Notes

Reaction equation

HRID 377374 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]=O.[CH:12]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:13].CCCCCCC.CCOC(C)=O>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1/[CH:10]=[CH:14]/[CH:12]=[O:13]

Participants

5

Reactant 3

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 7365001-Benzothiophene-2-carbaldehydeHCID 21899848Ethylacetate heptane

Product 1

HCID 19358673HCID 19358673, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzothiophene-2-carboxaldehyde (3 g, 18.4 mmol) and formylmethylenetriphenylphosphorane (5.62 g, 18.4 mmol) in CH2Cl2 (100 ml) was treated as seen in preparation 1. After a chromatography on silicagel (n-heptane/EtOAc 4/1) pure title compound was obtained (1.00 g, 5.31 mmol, yield 28.9%) as yellow crystals, m.p.=88°.

Workup

  1. customas seen in preparation 1

Sources & evidence

ORD record
ord-2088781e85054dd3a2d7d1f1be2f5826
Source dataset
uspto-grants-2000_02
Patent number
US06025390

Reaction notes

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