HCID 18954484, compound → HCID 18954485, compound

HRID 1492094Notes

Reaction equation

HRID 1492094 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:19])[CH2:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:7][C:6]=1[O:20][CH3:21])[CH:2]=[CH2:3].[H][H]>C(O)C.[Pd]>[CH3:21][O:20][C:6]1[CH:7]=[C:8]([C:11](=[O:19])[CH2:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=[CH:10][C:5]=1[O:4][CH2:1][CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 18954484HCID 18954484, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18954485HCID 18954485, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 50 ml eggplant type flask equipped with a magnetic stirrer, a dropping funnel, a reflux condenser and a gas-introducing tube was charged with 250 mg of a 5% palladium/carbon dispersed in 25 ml of ethanol and 5.0 g (24 mmol) of 1-(4-allyloxy-3-methoxyphenyl)-4,4-dimethylpentane-1,3-dione. After completely replacing the atmosphere of the reaction system with hydrogen, stirring was continued for 2 hours at room temperature. A light yellow oily material was obtained by removing the palladium/carbon by filtration and subsequently distilling off the solvent. Thereafter, the thus obtained oily material was subjected to silica gel column chromatography using hexane/ethyl acetate (10/1-5/1 (v/v)) as a developer to obtain 4.0 g (80% in yield) of the compound of interest, 1-(3-methoxy-4-propoxyphenyl)-4,4-dimethylpentane-1,3-dione, as an achromatic solid substance. This compound is hereinafter referred to as Compound (1d).

Workup

  1. customA 50 ml eggplant type flask equipped with a magnetic stirrer, a dropping funnel, a reflux condenser and a gas-introducing tube
  2. customA light yellow oily material was obtained
  3. customby removing the palladium/carbon
  4. filtrationby filtration
  5. distillationsubsequently distilling off the solvent
  6. customto obtain

Sources & evidence

ORD record
ord-b9931e24ebd740f6bc9d5ba58c342a59
Source dataset
uspto-grants-1994_12
Patent number
US05371296

Reaction notes

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