Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 21956511, compound

HRID 2213100Notes

Reaction equation

HRID 2213100 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH:5]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:2].[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1)[CH:31]=O>C(Cl)Cl>[CH3:26][O:27][C:28]1[CH:29]=[C:30](/[CH:31]=[CH:5]/[C:4]([O:3][CH2:1][CH3:2])=[O:25])[CH:33]=[CH:34][C:35]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 219565123-Methoxy-4-pyridin-2-ylbenzaldehyde

Product 1

HCID 21956511HCID 21956511, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl(triphenylphosphoranylidene)acetate (550 mg, 1.6 mmol) and 3-methoxy-4-pyridin-2-ylbenzaldehyde (225 mg, 1.1 mmol) were dissolved in CH2Cl2 (5 mL) and stirred at rt for 12 h. The reaction mixture was concentrated and purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 2:3) to afford the desired ethyl(2E)-3-(3-methoxy-4-pyridin-2-ylphenyl)prop-2-enoate.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:9 to 2:3)

Sources & evidence

ORD record
ord-16d5cf6f80ba4be0810740c32e6b139d
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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