Water → HCID 86688835, compound

Temperature

-78 °C

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).

1. customthe cooling bath is removed
2. stirringthe mixture is stirred at room temperature for a further hour
3. temperatureThe suspension is cooled −78° C.
4. additionis added
5. stirringThe mixture is stirred −78° C. for 1 h
6. customthe cooling bath is removed
7. stirringto stir at room temperature for a further 3 h
8. addition50 ml of n-hexane are added
9. customhydrolysis
10. washThe organic phase is washed three times with 50 ml of water
11. dry with materialdried over sodium sulfate
12. distillationAfter the solvents have been distilled off
13. customthe residue is dried under reduced pressure
14. customthe crude product (2.26 g, 88%) is used in the next stage without further purification

ORD record

ord-71720b71bd6541ec9bfeeb6c58029d6b

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09127020B2