Dichloromethane → HCID 57574460, compound

Participants

Reaction Conditions

Reaction Steps

1 mL POCl3 was added to a vigorously stirred solution of 4,4-dimethyl-4H-cyclopenta[2,1-b:3,4-b′]dithiophene (381.2 mg, 1.85 mmol) in 6 mL 5:1 CH2Cl2/DMF solvent mixture. The mixture was sealed in a pressure vessel and stirred at 100° C. for 10 min. The solution turned yellow then red upon cooling down. The reaction mixture was then basified with K2CO3 solution, stirred for 30 min more at room temperature to allow complete hydrolysis. The organic product was then extracted with CH2Cl2, concentrated, and purified by column chromatography (SiO2, CH2Cl2) to furnish a yellow oil that solidifies on standing (204 mg, 47%). Rf (silica gel, CH2Cl2)=0.41; 1H NMR (400 MHz, CDCl3): δ 1.50 (s, 6 H, 2 CH3), 7.05 (d, J=4.8 Hz, 1 H, ArH), 7.40 (d, J=4.8 Hz, 1 H, ArH), 7.63 (s, 1 H, ArH), 9.83 (s, 1 H, CHO); MS (EI): m/z=234 [M]+.

Provenance & Evidence