Water → HCID 86688835, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.1 g (5.0 mmol) of 4-propyl-4H-dithieno[3,2-b;2′,3′-d]pyrrole (32) in 17 ml of dry THF are added 6.9 ml (11.0 mmol) of a 1.6 M n-butyllithium/hexane solution at −78° C. After the mixture has been stirred at −78° C. for 1 h, the cooling bath is removed and the mixture is stirred at room temperature for a further hour. A precipitate forms during this time. The suspension is cooled −78° C. and a solution of 2.2 g (11.0 mmol) of trimethylstannyl chloride dissolved in 3 ml of THF is added. The mixture is stirred −78° C. for 1 h and then the cooling bath is removed to stir at room temperature for a further 3 h. 50 ml of n-hexane are added and hydrolysis is effected with water. The organic phase is washed three times with 50 ml of water and dried over sodium sulfate. After the solvents have been distilled off, the residue is dried under reduced pressure and the crude product (2.26 g, 88%) is used in the next stage without further purification. 1H NMR (CDCl3): 7.01 ppm (s, 2H), 4.16 (t, 2H), 1.94 (qa, 2H), 0.98 (t, 3H), 0.40 (s, 18H).

Provenance & Evidence