HCID 18954484, compound → HCID 18954485, compound

HRID 1613015Notes

Reaction equation

HRID 1613015 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].CCCCCC.C(OCC)(=O)C>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

6

Reactant 3

HCID 18954484HCID 18954484, compoundHCID 21226206Ethyl acetate hexaneHCID 178418361HCID 178418361, compound

Product 1

HCID 18954485HCID 18954485, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Into a 50 ml egg plant type flask equipped with a magnetic stirrer, a dropping funnel, a reflux condenser, and a nitogen-inlet tube, were charged 250 mg of 5% palladium/carbon and 5.0 gm (24 mmol) of 1-(4-allyloxy-3-methoxyphenyl)- 4,4-dimethylpentane-1,3-dione which had been dispersed in 25 ml of ethanol. After completely replacing the reaction atmosphere by hydrogen, the mixture was stirred for 2 hours at room temperature. Palladium/carbon was removed by filtration and the solvent was evaporated to obtain pale yellow oily product. The oil was submitted to silica gel column chromatography using a hexane-ethyl acetate (10:1-5:1) mixed solvent as an eluent to produce 4.0 gm (yield: 80%) of the title compound as a colorless solid.

Workup

  1. customInto a 50 ml egg plant type flask equipped with a magnetic stirrer, a dropping funnel, a reflux condenser, and a nitogen-inlet tube
  2. customPalladium/carbon was removed by filtration
  3. customthe solvent was evaporated
  4. customto obtain pale yellow oily product
  5. additionmixed solvent as an eluent

Sources & evidence

ORD record
ord-f5da25ca8e254788ae9079f83d642475
Source dataset
uspto-grants-1993_03
Patent number
US05191121

Reaction notes

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