Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → 3-(2-Ethoxycarbonylethenyl)-2-methyl-7-nitrobenzo[b]furan

HRID 342433Notes

Reaction equation

HRID 342433 reaction equation
[CH:1]([C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=2[O:6][C:7]=1[CH3:8])=O.[C:16]([CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:18][CH2:19][CH3:20])=[O:17]>O1CCOCC1>[CH2:19]([O:18][C:16]([CH:21]=[CH:1][C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=2[O:6][C:7]=1[CH3:8])=[O:17])[CH3:20]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 867535523-Formyl-2-methyl-7-nitrobenzo[b]furan

Product 1

HCID 702015513-(2-Ethoxycarbonylethenyl)-2-methyl-7-nitrobenzo[b]furanYield 84.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-formyl-2-methyl-7-nitrobenzo[b]furan (200 mg) and (carboethoxymethylene)triphenylphosphorane (434 mg) in dioxane (3 ml) was stirred at ambient temperature for 1 hour. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel. The obtained oil was crystallized from diisopropyl ether to give 3-(2-ethoxycarbonylethenyl)-2-methyl-7-nitrobenzo[b]furan (226 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography on silica gel
  3. customThe obtained oil was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-ef9c129ac1434376ae4f1fb958ae3d48
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

Loading…