Dimethylformamide → (5'-Chloro-[2,2']bithiophenyl-5-yl)-methanol

To a solution of 5-chloro-[2,2′]bithiophenyl (3.00 g, 14.9 mmol) in 30 mL of THF at 0° C. is added n-BuLi (9.8 mL of a 1.6M solution in hexanes, 15.7 mmol) dropwise. DMF (2.30 mL, 30 mmol) is added dropwise and the resulting solution is heated at reflux for 1 hour. The solution is diluted with H2O and extracted with Et2O. The organic layer is washed with H2O and saturated NaCl solution, then dried over MgSO4, filtered and concentrated. The crude aldehyde is dissolved in 40 mL of anhydrous MeOH and sodium borohydride (0.85 g, 22.5 mmol) is added portionwise. The mixture is stirred at room temperature for 10 min, then quenched with water. The mixture is diluted with Et2O and the layers separated. The organic layer is washed with H2O, then dried over MgSO4, filtered and concentrated to yield the title compound (2.23 g, 9.66 mmol) which is used in the subsequent step without further purification. 1H NMR (CDCl3, 300 MHz) δ6.95 (d, 1H), 6.90 (m, 2H), 6.86 (d, 1H), 4.82 (s, 2H), 1.88 (bs, 1H).

1. temperaturethe resulting solution is heated
2. temperatureat reflux for 1 hour
3. extractionextracted with Et2O
4. washThe organic layer is washed with H2O and saturated NaCl solution
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. dissolutionThe crude aldehyde is dissolved in 40 mL of anhydrous MeOH
9. customquenched with water
10. additionThe mixture is diluted with Et2O
11. customthe layers separated
12. washThe organic layer is washed with H2O
13. dry with materialdried over MgSO4
14. filtrationfiltered
15. concentrationconcentrated

ORD record

ord-04630d7c61914b28a6440c7da6fd3375

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612075B2