Thionyl Chloride → 6,7-Dihydro-1-benzothiophen-5(4H)-one
Reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][C:9](O)=O.S(Cl)(Cl)=[O:13]>>[O:13]=[C:8]1[CH2:9][C:3]2[CH:4]=[CH:5][S:1][C:2]=2[CH2:6][CH2:7]1Participants
Procedure
4-(2-Thienyl)butyric acid was reacted with thionyl chloride and stannic chloride to provide 5-oxo-4,5,6,7-tetrahydrobenzothiophene, which upon reaction with hydrazine and sodium hyroxide gave 4,5,6,7-tetrahydrobenzothiophene. A solution of 13.3 g of 4,5,6,7-tetrahydrobenzothiophene in 150 ml of dichloromethane was added dropwise to a stirred suspension of 13.1 g of ethyl oxalyl chloride and 14.0 g of aluminum chloride in 200 ml of dichloromethane. The reaction mixture was stirred for twelve hours at 25° C. following the addition. The reaction mixture was poured into 500 g of ice and then the organic layer was separated, dried, and the solvent was removed by evaporation to give 19.2 g of ethyl α-oxo-α-(4,5,6,7-tetrahydro-2-benzothienyl)acetate.
Sources & evidence
- ORD record
- ord-5d45a16353b4424aa185c334d82e7929
- Source dataset
- uspto-grants-1984_11
- Patent number
- US04482553
Reaction notes
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