Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 86742583, compound

HRID 1110587Notes

Reaction equation

HRID 1110587 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[C:8](/[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:9]/[CH:10]=O)[CH:5]=[CH:6][CH:7]=1.[C:17]([CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:19][CH3:20])=[O:18]>ClCCl>[CH3:20][O:19][C:17](=[O:18])/[CH:21]=[CH:10]/[CH:9]=[C:8](/[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)\[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 14994121HCID 14994121, compound

Product 1

HCID 86742583HCID 86742583, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As described in Example 99, (E)-3-(3-fluorophenyl)-2-octenal (5.43 g) was treated with (carbomethoxymethylene)triphenylphosphorane (9 g) in dichloromethane (50 mL) for 4 days at room temperature. The ester was isolated in the usual manner and purified by HPLC (ether-hexane; 1:9) to provide 6.04 g of (E,E)-5-(3-fluorophenyl)-2,4-decadienoic acid methyl ester as an oil.

Sources & evidence

ORD record
ord-7687e0ae34834bf9a39d89abd695e386
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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