HCID 54027451, compound → 1,3-Cyclohexanedione, 2-(3-(1,3-benzodioxol-5-yl)-1-oxopropyl)-5-phenyl-

HRID 905046Notes

Reaction equation

HRID 905046 reaction equation
[C:1]1([CH:7]2[CH2:12][C:11](=[O:13])[CH:10]([C:14](=[O:26])[CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]4[O:23][CH2:24][O:25][C:19]=4[CH:18]=3)[C:9](=[O:27])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>O1CCCC1.[C].[Pd]>[C:1]1([CH:7]2[CH2:12][C:11](=[O:13])[CH:10]([C:14](=[O:26])[CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]4[O:23][CH2:24][O:25][C:19]=4[CH:18]=3)[C:9](=[O:27])[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 54027451HCID 54027451, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 30597141,3-Cyclohexanedione, 2-(3-(1,3-benzodioxol-5-yl)-1-oxopropyl)-5-phenyl-

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In 200 ml of tetrahydrofuran was dissolved 10.8 g of 5-phenyl-2-[3-(3,4-methylenedioxyphenyl)-propenoyl]-cyclohexane-1,3-dione prepared in step (1) above, and 2 g of a 5% palladium-carbon catalyst was added to the solution and catalytic reduction was carried out for 7 hours with hydrogen under atmospheric pressure. The catalyst was removed by filtration and tetrahydrofuran was removed by distillation. Recrystallization from isopropyl alcohol have 7.5 g (the yield being 70%) of the desired 5-phenyl-2-[3-(3,4-methylenedioxyphenyl)-propionyl]-cyclohexane-1,3-dione.

Workup

  1. additionwas added to the solution and catalytic reduction
  2. customThe catalyst was removed by filtration and tetrahydrofuran
  3. customwas removed by distillation
  4. customRecrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-a99c6563587848629cd22f2c7e4b2ea5
Source dataset
uspto-grants-1983_12
Patent number
US04421763

Reaction notes

Loading…