Dimethylformamide → 1-(5-Formylthiophen-2-yl)cyclopent-3ene carboxylic acid ethyl ester
Reaction equation
O=P(Cl)(Cl)Cl.[CH2:6]([O:8][C:9]([C:11]1([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]=[CH:13][CH2:12]1)=[O:10])[CH3:7].CN([CH:24]=[O:25])C>>[CH2:6]([O:8][C:9]([C:11]1([C:16]2[S:17][C:18]([CH:24]=[O:25])=[CH:19][CH:20]=2)[CH2:15][CH:14]=[CH:13][CH2:12]1)=[O:10])[CH3:7]Participants
4
Conditions
- Temperature
- 105 °C
Procedure
POCl3 (275 mg, 1.8 mmol) was added to 1 ml DMF at ambient temperature and stirred for 30 minutes. The product of Step 1, above (2) (208 mg, 0.93 mmol), was dissolved in 1 ml DMF, added to the reaction mixture and stirred for 1 hour at ambient temperature. The reaction mixture was heated to 105° C. for 3 hours, cooled to ambient temperature, quenched with saturated sodium acetate solution and extracted (2×10 ml, EtOAc). The organics were washed with brine and dried over MgSO4, filtered and concentrated to yield the title compound (3).