Thiophene → 2-(7-Methoxycarbonyl-1-oxoheptyl)thiophene

HRID 2254324Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O.ClCC(OC(=O)CCl)=O.[S:23]1[CH:27]=[CH:26][CH:25]=[CH:24]1>ClC(Cl)C>[CH3:1][O:2][C:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([C:24]1[S:23][CH:27]=[CH:26][CH:25]=1)=[O:12])=[O:13]

Participants

Conditions

Temperature: 60 °C

Procedure

In 50 ml of dichloroethane were dissolved 9.41 g (0.05 mole) of suberic acid monomethyl ester 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 60° C. for 5 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 11.5 g of 2-(7-methoxycarbonyl-1-oxoheptyl)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-3c9d73751140432cab76c4d321254801
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05235068

Reaction notes

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