Acetic Anhydride → Methyl 3-(2-acetylthiophen-3-yl)benzoate

HRID 1740295ノート

反応式

HRID 1740295 の反応式
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=2)[C:9]([O:11][CH3:12])=[O:10])=[CH:2]1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[C:16]([C:2]1[S:1][CH:5]=[CH:4][C:3]=1[C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:18])[CH3:17]

参加物

3

反応物 2

HCID 7918Acetic AnhydrideHCID 3564198Methyl 3-(3-thienyl)benzoate

生成物 1

HCID 21838227Methyl 3-(2-acetylthiophen-3-yl)benzoate収率 60.4%

反応条件

温度
75 °C

実験手順

A mixture of methyl 3-(thiophen-3-yl)benzoate (2 g) in acetic anhydride (2 g) was heated to 75° C. The oil bath was removed and phosphoric acid (0.063 ml) was added thereto. The reaction mixture was stirred at 140° C. for 2 hours and cooled to room temperature. The mixture was diluted with ethyl acetate and washed successively with water, an aqueous sodium carbonate solution (×2) and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of hexane:ethyl acetate (10:1) to afford methyl 3-(2-acetylthiophen-3-yl)benzoate (1.44 g).

後処理

  1. customThe oil bath was removed
  2. additionphosphoric acid (0.063 ml) was added
  3. temperaturecooled to room temperature
  4. additionThe mixture was diluted with ethyl acetate
  5. washwashed successively with water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel eluting with a mixture of hexane:ethyl acetate (10:1)

出典と根拠

ORDレコード
ord-3dc5a2ba29db4f0b9a84aeffc7ce342a
出典データセット
uspto-grants-1999_10
特許番号
US05968985

反応ノート

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