Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 14652665, compound

HRID 1164822Notes

Reaction equation

HRID 1164822 reaction equation
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:25][C:26]1[C:31]([CH:32]=O)=[C:30]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:29]=[CH:28][N:27]=1>C(Cl)Cl>[CH3:24][O:23][C:21](=[O:22])/[CH:20]=[CH:32]/[C:31]1[C:26]([CH3:25])=[N:27][CH:28]=[CH:29][C:30]=1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 14652664HCID 14652664, compound

Product 1

HCID 14652665HCID 14652665, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl (triphenylphosphoranylidene)acetate (30 g) was added to a stirred mixture of 16.0 g (0.081 mol) of 2-methyl-4-phenyl-3-pyridinecarboxaldehyde in 300 ml of methylene chloride. The resulting mixture was stirred at room temperature for 18 hours, after which the mixture was filtered through silica gel and the filtrate concentrated under vacuum. The residue was chromatographed on a silica gel column, eluting with ethyl acetate to yield 18.9 g of (E)-methyl-3-(2-methyl-4-phenyl-3-pyridinyl)-2-propenoate.

Workup

  1. filtrationafter which the mixture was filtered through silica gel
  2. concentrationthe filtrate concentrated under vacuum
  3. customThe residue was chromatographed on a silica gel column
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-58a9f007a32f477dbb4606f221cec0bb
Source dataset
uspto-grants-1990_03
Patent number
US04906624

Reaction notes

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