HCID 84740921, compound → HCID 77230809, compound

Participants

Reaction Steps

To a reaction flask containing 2,6-dichlorothieno[2,3-b]pyridine-5-carbaldehyde (5.1 g, 21.97 mmol) in 300 mL of THF at −20° C. was added methylmagnesium chloride, 3.0M solution in tetrahydrofuran (7.69 mL, 23.07 mmol) dropwise. After 1 h, an additional charge of 0.7 mL of MeMgCl was added. After 15 min, the reaction was quenched by the addition of 50 mL sat. NH4Cl and 50 mL water. After warming to rt, ethyl acetate was added and the organic layer was separated and washed with water and brine. The organic layer was dried over MgSO4, filtered, and concentrated to afford 1-(2,6-dichlorothieno[2,3-b]pyridin-5-yl)-ethanol. 1H NMR (400 MHz, CDCl3) δ 8.19 (d, J=0.8 Hz, 1H), 7.14 (s, 1H), 5.32 (qdd, J=6.3, 3.5, 0.8 Hz, 1H), 2.07 (J=3.5 Hz, 1H), 1.56 (d, J=6.6 Hz, 3H) ppm.

Provenance & Evidence