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

HRID 1740295Notes

Reaction equation

HRID 1740295 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
75 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-3dc5a2ba29db4f0b9a84aeffc7ce342a
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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