Thiophene → 2-(3,4,5-Trimethoxybenzoyl)thiophene

HRID 2254335

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.ClCC(OC(=O)CCl)=O.[S:25]1[CH:29]=[CH:28][CH:27]=[CH:26]1>ClC(Cl)C>[CH3:15][O:14][C:10]1[CH:9]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:11]=1[O:12][CH3:13])[C:6]([C:26]1[S:25][CH:29]=[CH:28][CH:27]=1)=[O:8]

Participants

Conditions

Temperature: 65 °C

Procedure

In 50 ml of dichloroethane were dissolved 10.6 g (0.05 mole) of 3,4,5-trimethoxybenzoic acid and 9.83 g (0.0575 mole) of monochloroacetic anhydride. To the resulting solution were added 5.47 g (0.065 mole) of thiophene and 0.71 g of boron trifluoride-diethyl ether complex and the resulting mixture was then stirred at 65° C. for 6 hours. After completion of the reaction, the reaction solution was cooled and washed successively with water, 5% aqueous sodium carbonate solution and water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 5.77 g of 2-(3,4,5-trimethoxybenzoyl)thiophene.

Workup

customAfter completion of the reaction
temperaturethe reaction solution was cooled
washwashed successively with water, 5% aqueous sodium carbonate solution and water
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f732a69611604ab9a29d41118ece847c
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05235068

Linked notes

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