Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → (E)-3-(6-methoxy-3-pentylbenzofuran-2-yl)-2-propenoic acid methyl ester

HRID 1651270Notes

Reaction equation

HRID 1651270 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[C:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[C:8]([CH:10]=O)[O:9][C:5]=2[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]>ClCCl>[CH3:22][O:21][C:19](=[O:20])/[CH:23]=[CH:10]/[C:8]1[O:9][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:18]=[CH:17][C:6]=2[C:7]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 147427736-Methoxy-3-pentyl-2-benzofurancarboxaldehyde

Product 1

HCID 14742791(E)-3-(6-methoxy-3-pentylbenzofuran-2-yl)-2-propenoic acid methyl esterYield 76.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 111, 6-methoxy-3-pentyl-2-benzofurancarboxaldehyde (4.82 g) and (carbomethoxymethylene)triphenylphosphorane (6.7 g) in dichloromethane (75 mL) was stirred at room temperature for 42 hours. Purification of the crude reaction product by HPLC (diethyl ether-hexane; 1:12) gave 4.55 g of (E)-3-(6-methoxy-3-pentylbenzofuran-2-yl)-2-propenoic acid methyl ester as an oil.

Workup

  1. customPurification of the crude
  2. customreaction product by HPLC (diethyl ether-hexane; 1:12)

Sources & evidence

ORD record
ord-57fb68fcd4054cc9baebdb4ddad14b9f
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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