HCID 19010813, compound → HCID 19010736, compound

HRID 1741838Notes

Reaction equation

HRID 1741838 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[C:10]([CH3:12])[CH3:11])[CH:6]=[CH:5][C:4]=1[C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17]>[Pd]>[CH2:9]([C:7]1[CH:6]=[CH:5][C:4]([CH:13]([OH:18])[CH2:14][CH2:15][CH2:16][CH3:17])=[C:3]([O:2][CH3:1])[CH:8]=1)[CH:10]([CH3:12])[CH3:11]

Participants

3

Reactant 1

HCID 19010813HCID 19010813, compound

Product 1

HCID 19010736HCID 19010736, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 2'-methoxy-4'-(2-methyl-1-propenyl)valerophenone (88 mg) and 10% palladium on carbon (30 mg) was stirred under hydrogen atmosphere for 30 minutes. Catalyst was removed by filtration and the filtrate was concentrated. The residue was dissolved in methanol (5 ml) and then sodium borohydride (16 mg) was added. The reaction mixture was stirred at room temperature for 30 minutes. The mixture was poured into ice water and acidified with 6N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated to give 1-(4-isobutyl-2-methoxyphenyl)pentanol (88 mg) as an oil.

Workup

  1. customCatalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in methanol (5 ml)
  4. additionsodium borohydride (16 mg) was added
  5. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  6. additionThe mixture was poured into ice water
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with water and brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-4fe0070c9d9b4f1dbe277653f92ae6c5
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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