Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 14347274, compound

HRID 2232812Notes

Reaction equation

HRID 2232812 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=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]>C(Cl)(Cl)(Cl)Cl.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:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 14547230HCID 14547230, compound

Product 1

HCID 14347274HCID 14347274, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

As described in Example 99, (Z)-3-(4-methoxyphenyl)-3-phenyl-2-propenal (7.3 g) was treated with (carbomethoxymethylene)triphenylphosphorane (11.9 g) in carbon tetrachloride (50 mL) and dichloromethane (10 mL) overnight at room temperature. The crude ester was isolated in the usual way and purified by HPLC (ether-hexane; 1:7.5) to furnish 6.4 g of (2E,4Z)-5-(4-methoxyphenyl)-5-phenyl-2,4-pentadienoic acid methyl ester as an oil.

Workup

  1. customThe crude ester was isolated in the usual way
  2. custompurified by HPLC (ether-hexane; 1:7.5)

Sources & evidence

ORD record
ord-5a091c18fd3a4370b7b7f59f12962e48
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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