Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 14347270, compound

HRID 2232809Notes

Reaction equation

HRID 2232809 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:10]\[CH:11]=O)=[CH:5][CH:4]=1.[C:19]([CH:23]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:21][CH3:22])=[O:20]>ClCCl>[CH3:22][O:21][C:19](=[O:20])/[CH:23]=[CH:11]/[CH:10]=[C:9](\[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)/[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 14994116HCID 14994116, compound

Product 1

HCID 14347270HCID 14347270, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As described in Example 99, (E)-3-(4-methoxyphenyl)-3-(3- pyridinyl)-2-propenal (5.25 g was reacted with (carbomethoxymethylene)triphenylphosphorane (7.4 g) in dichloromethane (40 mL) for 17 hours at room temperature. The crude ester was isolated in the usual way and was purified by HPLC to give 4.6 g of the ester. A portion was crystallized twice from ether-hexane to give the analytical sample of (E,E)-5-(4-methoxyphenyl)-5-(3-pyridinyl)-2,4-pentadienoic acid methyl ester, mp 75°-76° C.

Workup

  1. customThe crude ester was isolated in the usual way
  2. customwas purified by HPLC

Sources & evidence

ORD record
ord-1b3c0578cc0a4400b44237d9f3a814e3
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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