3-[4-(3-Hydroxy-prop-1-ynyl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one → 3-[4-(3-Hydroxy-propyl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

HRID 1617522Notes

Reaction equation

HRID 1617522 reaction equation
[OH:1][CH2:2][C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH2:12][C:13]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=2)=[O:14])=[CH:7][CH:6]=1>C(OCC)(=O)C.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH2:12][C:13]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=2)=[O:14])=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 666687223-[4-(3-Hydroxy-prop-1-ynyl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

Product 1

HCID 670155883-[4-(3-Hydroxy-propyl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-oneYield 101.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-[4-(3-Hydroxy-prop-1-ynyl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one (example 85, step 1; 40 mg) in ethyl acetate (6 mL) was hydrogenated in the presence of Pd (5% on carbon, 7 mg) at room temperature for 1.5 hours. The solution was filtered over decalite, the filter residue was washed with ethyl acetate, and the solution was evaporated to yield 3-[4-(3-hydroxy-propyl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one (41 mg, 64%) as a colorless oil, which was directly subjected to the next step.

Workup

  1. filtrationThe solution was filtered over decalite
  2. washthe filter residue was washed with ethyl acetate
  3. customthe solution was evaporated

Sources & evidence

ORD record
ord-f0f17e0a55bd45fa9c77315d4bb16254
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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