Dimethylformamide → 2-phenyl-6,7-dihydro-1-benzofuran-4(5H)-one

HRID 1606180Notes

Reaction equation

HRID 1606180 reaction equation
CN(C)[CH:3]=[O:4].[CH2:6](Br)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8]>O>[O:4]=[C:3]1[C:6]2[CH:6]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:8][C:7]=2[CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 6228Dimethylformamide2×HCID 6259Phenacyl bromide

Product 1

HCID 100590252-phenyl-6,7-dihydro-1-benzofuran-4(5H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5.0 g. of 3-(1-pyrrolodinyl)-2-cyclohexan-1-one in 30 ml. of anhydrous dimethylformamide is treated dropwise over twenty minutes under nitrogen with a solution of 6.0 g. of phenacyl bromide in 10 ml. of anhydrous dimethylformamide. The mixture is stirred for 47 hours at 80°C., allowed to cool to ambient temperature, and then poured into water and stirred for 30 minutes. The resulting suspension is extracted with chloroform, the chloroform extracts are combined, washed with water and dried. The solvent is removed and the residue is dried under high vacuum and crystallized from ethanol to yield 4-oxo-2-phenyl-4,5,6,7-tetrahydrobenzo[b]furan, m.p. 132°-134°C.

Workup

  1. temperatureto cool to ambient temperature
  2. stirringstirred for 30 minutes
  3. extractionThe resulting suspension is extracted with chloroform
  4. washwashed with water
  5. customdried
  6. customThe solvent is removed
  7. customthe residue is dried under high vacuum
  8. customcrystallized from ethanol

Sources & evidence

ORD record
ord-29c8b596c7b04c10b47ce422a763b1ef
Source dataset
uspto-grants-1976_04
Patent number
US03952025

Reaction notes

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