Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 14347284, compound

HRID 1110569Notes

Reaction equation

HRID 1110569 reaction equation
[CH:1]1(/[C:7](/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:8]/[CH:9]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]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:9]/[CH:8]=[C:7](/[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)\[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 14547241HCID 14547241, compound

Product 1

HCID 14347284HCID 14347284, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

As in Example 99, (Z)-3-cyclohexyl-3-(4-methoxyphenyl)-2-propenal (7.3 g) was reacted with (carbomethoxymethylene)triphenylphosphorane (11 g) in carbon tetrachloride (40 mL) and dichloromethane (4 mL) overnight at room temperature. The crude ester, isolated in the normal fashion, was purified by HPLC (ether-hexane; 1:7) to yield 5.7 g of (2E,4Z)-5-cylcohexyl-5-(4-methoxyphenyl)-2,4-pentadienoic acid methyl ester. A portion was crystallized from hexane to give the analytical specimen, mp 70.5°-72° C.

Workup

  1. customThe crude ester, isolated in the normal fashion
  2. customwas purified by HPLC (ether-hexane; 1:7)

Sources & evidence

ORD record
ord-a4e2aee53c21440ebeca03bb909b58f5
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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