4-(4-Methoxy-3-methylphenyl)but-3-yn-1-ol → 4-(4-Methoxy-3-methylphenyl)butan-1-ol

HRID 499011Notes

Reaction equation

HRID 499011 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH2:11][CH2:12][OH:13])=[CH:5][C:4]=1[CH3:14]>[Pd].CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[CH:5][C:4]=1[CH3:14]

Participants

4

Reactant 1

HCID 607996814-(4-Methoxy-3-methylphenyl)but-3-yn-1-ol

Product 1

HCID 282961584-(4-Methoxy-3-methylphenyl)butan-1-olYield 55.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

This compound was prepared in a manner analogous to that of Step E of Example 1, by the hydrogenation of 1.4 grams (0.0074 mole) of 4-(4-methoxy-3-methylphenyl)but-3-yn-1-ol in the presence of 0.05 gram (catalyst) of 10% palladium on carbon in 150 mL of methanol. The reaction product was purified by column chromatography on silica gel using mixtures of hexane and ethyl acetate as an eluant. The appropriate fractions of eluate were combined and concentrated under reduced pressure, yielding 0.8 gram of subject compound. The NMR spectrum was consistent with the proposed structure. This reaction was repeated on a larger scale.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step E of Example 1
  2. customThe reaction product was purified by column chromatography on silica gel using mixtures of hexane and ethyl acetate as an eluant
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a8edd48dfa454fd18b744ca9da6aa22c
Source dataset
uspto-grants-2010_08
Patent number
US07767667B2

Reaction notes

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