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

HRID 6490

反応式

HRID 6490 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-49f779f24ab24cde9206b27accb4fa10
出典データセット
uspto-grants-1993_09
特許番号
US05248825

関連ノート

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