(Triphenylphosphoranylidene)acetaldehyde → HCID 6479252, compound

HRID 377379Notes

Reaction equation

HRID 377379 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[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>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:15]/[CH:13]=[O:14]

Participants

5

Reactant 3

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 796192-QuinolinecarboxaldehydeHCID 21899848Ethylacetate heptane

Product 1

HCID 6479252HCID 6479252, compoundYield 11.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of quinolin-2-carboxaldehyde (3.5 g, 22.3 mmol) and formylmethylenetriphenylphosphorane (6.79 g, 22.3 mmol) in CH2Cl2 (180 ml) was treated as seen in preparation 1. After a chromatography on silicagel (n-heptane/EtOAc 4/1) pure title compound was obtained (460 mg, 2.51 mmol, yield 11.3%) as grey needles, m.p.=85°.

Workup

  1. customas seen in preparation 1

Sources & evidence

ORD record
ord-1cea6b2bc2f54058a837a497be762435
Source dataset
uspto-grants-2000_02
Patent number
US06025390

Reaction notes

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