Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 3-[4-(4-pyridinyl)-6-quinolinyl]-2-propenoate

HRID 1625969Notes

Reaction equation

HRID 1625969 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=O)[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.C1(P(=[CH:38][C:39]([O:41][CH3:42])=[O:40])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=[CH:38][C:39]([O:41][CH3:42])=[O:40])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 598600984-(4-Pyridinyl)-6-quinolinecarboxaldehyde

Product 1

HCID 66781544Methyl 3-[4-(4-pyridinyl)-6-quinolinyl]-2-propenoateYield 95.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(4-pyridinyl)-6-quinolinecarbaldehyde (2.29 g, 9.78 mmol), methyl (triphenylphosphoranylidene)acetate (3.30 g, 9.78 mmol) in MeOH (75 mL) was stirred at room temperature for 1 hour. The reaction was evaporated under reduced pressure and the resulting residue was purified by silica gel chromatography (1% MeOH in EtOAc) to give the title compound (2.71 g, 95%) as a white solid. MS(ES)+ m/e 291 [M+H]+.

Workup

  1. customThe reaction was evaporated under reduced pressure
  2. customthe resulting residue was purified by silica gel chromatography (1% MeOH in EtOAc)

Sources & evidence

ORD record
ord-b1d034d7d390446b8944886f1843be99
Source dataset
uspto-grants-2014_07
Patent number
US08785433B2

Reaction notes

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