Phenylacetylene → 1-(3,4,5-Trimethoxyphenyl)-3-phenyl-2-propyne-1-one

HRID 6490

Reaction equation

HRID 6490 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li].[C:11]1([C:17]#[CH:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CON(C)[C:22](=[O:35])[C:23]1[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=1>O1CCCC1>[CH3:30][O:29][C:27]1[CH:28]=[C:23]([C:22](=[O:35])[C:18]#[C:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:24]=[C:25]([O:33][CH3:34])[C:26]=1[O:31][CH3:32]

Participants

5

Reactant 3

HCID 10821PhenylacetyleneHCID 267535N,3,4,5-tetramethoxy-N-methyl-BenzamideHCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 147633891-(3,4,5-Trimethoxyphenyl)-3-phenyl-2-propyne-1-oneYield 34.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Place lithium hexamethyldisilazane (3 mL of a 1M solution in tetrahydrofuran, 3 mmol) and tetrahydrofuran (10 mL) under an argon atmosphere and cool to 0° C. Add phenylacetylene (0.33 mL, 3 mmol) and stir at 0° C. for 30 minutes. Add N-methoxy-N-methyl-(3,4,5-trimethoxy)benzamide (0.76 g, 3 mmol), remove the cooling bath and stir at room temperature for 1 hour. Partition between ethyl ether and saturated aqueous sodium chloride, separate the organic phase and dry (MgSO4). Filter and evaporate the solvent in vacuo. Pour onto silica gel and elute with 20% ethyl acetate/hexane to yield a crude solid. Recrystallize (hexane/ethyl acetate) to yield 0.31 g of the title compound; mp 94°-96° C.

Workup

  1. customPartition between ethyl ether and saturated aqueous sodium chloride
  2. customseparate the organic phase
  3. dry with materialdry (MgSO4)
  4. filtrationFilter
  5. customevaporate the solvent in vacuo
  6. additionPour onto silica gel
  7. washelute with 20% ethyl acetate/hexane
  8. customto yield a crude solid
  9. customRecrystallize (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-49f779f24ab24cde9206b27accb4fa10
Source dataset
uspto-grants-1993_09
Patent number
US05248825

Linked notes

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