Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 86742585, compound

HRID 1110591Notes

Reaction equation

HRID 1110591 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:9]/[CH:10]=O)=[CH:4][CH:3]=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:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)\[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 86742586HCID 86742586, compound

Product 1

HCID 86742585HCID 86742585, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As described in Example 99, (E)-3-(4-fluorophenyl)-2-octenal (7.4 g) was treated with (carbomethoxymethylene)triphenylphosphorane (13.5 g) in dichloromethane (60 mL) for 4 days at room temperature. The ester was isolated in the normal manner and purified by HPLC (ether-hexane; 1:9) to yield 7.04 g of (E,E)-5-(4-fluorophenyl)-2,4-decadienoic acid methyl ester as an oil.

Sources & evidence

ORD record
ord-3a388097629a4bebb150f9a6deb4e7ed
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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