Water → HCID 57054583, compound

HRID 978314Notes

Reaction equation

HRID 978314 reaction equation
[O:1]1[C:5]([CH:6]=O)=[CH:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:19][C:20](=[O:22])[CH3:21])C=CC=CC=1.O>CS(C)=O>[O:1]1[C:5]([CH:6]=[CH:19][C:20](=[O:22])[CH3:21])=[CH:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 150381-(Triphenylphosphoranylidene)acetoneHCID 613412-Benzofurancarboxaldehyde

Product 1

HCID 57054583HCID 57054583, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of benzo[b]furan-2-carboxaldehyde (3.3 g) and 1-triphenylphosphoranylidene-2-propanone (1.2 equivalents) in dimethyl sulfoxide (180 ml) was stirred at a temperature of 35° C. for a period of 30 minutes. The cooled mixture was poured into water and the aqueous mixture was extracted with diethyl ether. The solvent was evaporated from the dried (MgSO4) fraction and the residue was purified by column chromatography over silica gel (dichloromethane elution) to give 1-(benzo[b]furan-2-yl)but-1-en-3-one (3.0 g) as an orange solid, mp 100°-101° C.

Workup

  1. extractionthe aqueous mixture was extracted with diethyl ether
  2. customThe solvent was evaporated from the
  3. dry with materialdried (MgSO4) fraction
  4. customthe residue was purified by column chromatography over silica gel (dichloromethane elution)

Sources & evidence

ORD record
ord-83cc29c84c0649f1a3ca1d00d4eebadb
Source dataset
uspto-grants-1987_05
Patent number
US04664693

Reaction notes

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