p-Chlorophenacyl bromide → 4-(p-Chlorophenyl)dihydrofuran-2(3H)-one

HRID 65259Notes

Reaction equation

HRID 65259 reaction equation
[K].[C:2]([O:8][CH3:9])(=[O:7])[CH2:3][C:4]([O-])=O.[Cl:10][C:11]1[CH:20]=[CH:19][C:14](C(=O)CBr)=[CH:13][CH:12]=1.C([O-])(=O)C.[NH4+].[BH4-].[Na+]>C(O)(=O)C.CS(C)=O>[Cl:10][C:11]1[CH:20]=[CH:19][C:14]([CH:4]2[CH2:9][O:8][C:2](=[O:7])[CH2:3]2)=[CH:13][CH:12]=1

Participants

8

Reactant 5

HCID 68303p-Chlorophenacyl bromideHCID 517165Ammonium AcetateHCID 3801157Monomethyl malonateHCID 4311764Sodium borohydrideHCID 5462222Potassium

Product 1

HCID 30152944-(p-Chlorophenyl)dihydrofuran-2(3H)-oneYield 71%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

To 204 ml of dimethyl sulfoxide were added 40.1 g of potassium salt of monomethyl malonate (XVI) and then 50.0 g of p-chlorophenacyl bromide (XVII), and the mixture was stirred at room temperature for 30 minutes. Then, 12.9 g of ammonium acetate were added and the mixture was stirred at room temperature for 2 hours. Subsequently, 36.6 ml of acetic acid were added and 8.5 g of sodium borohydride were added under ice-cooling over one hour. The reaction mixture was allowed to stand at room temperature for one hour to reduce the double bond. After 68 ml of ice-water were added, the mixture was heated under reflex at 125°-130° C. for 3 hours to effect decarboxylation. After completion of the reaction, the reaction mixture was poured into 500 ml of ice-water, the black precipitate thus separated was collected by filtration and subjected to distillation under reduced pressure to give 29.7 g of the title compound (yield 71%).

Workup

  1. temperaturecooling over one hour
  2. waitto stand at room temperature for one hour
  3. temperaturethe mixture was heated under reflex at 125°-130° C. for 3 hours
  4. customAfter completion of the reaction
  5. customthe black precipitate thus separated
  6. filtrationwas collected by filtration
  7. distillationsubjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-35d55c900f194b2c836007d68c4db2ac
Source dataset
uspto-grants-1986_09
Patent number
US04613613

Reaction notes

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