Ethyl Acetate → (R)-3-(4-Ethynyl-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

HRID 1617817Notes

Reaction equation

HRID 1617817 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:30])[CH2:9][C@@H:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[C:11]2[CH:16]=[CH:15][C:14]([C:17]#[C:18][Si](C)(C)C)=[CH:13][CH:12]=2)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+].C(OCC)(=O)C>CO>[C:17]([C:14]1[CH:13]=[CH:12][C:11]([C@H:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[CH2:9][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=2)=[O:30])=[CH:16][CH:15]=1)#[CH:18]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 67015635(R)-1-(2-Methyl-pyridin-4-yl)-3-o-tolyl-3-(4-trimethylsilanylethynyl-phenyl)-propan-1-one

Product 1

HCID 86661100(R)-3-(4-Ethynyl-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-oneYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-3-(4-trimethylsilanylethynyl-phenyl)-propan-1-one (100 mg) in methanol (5 mL) was added at 0° C. potassium carbonate (3.4 mg). The reaction mixture was stirred at room temperature for 20 h. A saturated aq. solution of ammonium chloride and ethyl acetate were added, the phases were separated and the inorganic one was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (15% to 50% ethyl acetate in n-heptane) to yield the title compound as a colourless oil (60 mg, 95%), MS (ESI+): m/z=340.2 ([M+H]+).

Workup

  1. customthe phases were separated
  2. extractionthe inorganic one was extracted with ethyl acetate (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel (15% to 50% ethyl acetate in n-heptane)

Sources & evidence

ORD record
ord-ba0d91ecd2a244f18ec08c46ce623ef1
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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