Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 86742579, compound

HRID 1110579Notes

Reaction equation

HRID 1110579 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[CH2:13][CH2:14][CH2:15][CH3:16])=[CH:10]/[CH:11]=O)=[CH:5][CH:4]=1.[C:17]([CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:19][CH3:20])=[O:18]>C(Cl)(Cl)(Cl)Cl.ClCCl>[CH3:20][O:19][C:17](=[O:18])/[CH:21]=[CH:11]/[CH:10]=[C:9](/[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)\[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 14547236HCID 14547236, compound

Product 1

HCID 86742579HCID 86742579, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

As described in Example 99, (E)-3-(4-methoxyphenyl)-2-heptenal (10 g) was treated with (carbomethoxymethylene)triphenylphosphorane (17 g) in carbon tetrachloride (70 mL) and dichloromethane (15 mL) for 4 days at room temperature. The ester was isolated in the normal way and purified by HPLC (ether-hexane; 1:9) to furnish 8 g of (E,E)-5-(4-methoxyphenyl)-2,4-nonadienoic acid methyl ester, as an oil.

Sources & evidence

ORD record
ord-e1e51610de3b4c0dbd5d8d8ad2232ba7
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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