Acetone → 7-fluoro-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

HRID 1517640Notes

Reaction equation

HRID 1517640 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[OH:11])=[O:3].[CH3:12][C:13]([CH3:15])=O.N1CCCC1>C1(C)C=CC=CC=1.CCOCC>[F:10][C:7]1[CH:6]=[C:5]2[C:4]([C:2](=[O:3])[CH2:1][C:13]([CH3:15])([CH3:12])[O:11]2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 31268PyrrolidineHCID 27373264'-Fluoro-2'-hydroxyacetophenone

Product 1

HCID 152053737-fluoro-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-fluoro-2-hydroxyacetophenone (Aldrich, 1.54 g, 10 mmol), acetone (0.95 mL, 12.9 mmol), and pyrrolidine (0.83 mL, 9.94 mmol) was stirred in 3 mL toluene at room temperature for 1 h and at reflux (Dean-Stark trap) for 4 hours. After cooling to room temperature, the mixture was diluted with ether (30 mL) and was washed with 2N HCl (10 mL) and H2O (10 mL). Drying over Na2SO4 and evaporation of volatiles in vacuo afforded the crude title compound, which was used without further purification.

Workup

  1. temperatureat reflux (Dean-Stark trap) for 4 hours
  2. washwas washed with 2N HCl (10 mL) and H2O (10 mL)
  3. dry with materialDrying over Na2SO4 and evaporation of volatiles in vacuo

Sources & evidence

ORD record
ord-ebc689b90ac94daf8363508181e66cd9
Source dataset
uspto-grants-2012_07
Patent number
US08232309B2

Reaction notes

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