Tetrahydrofuran → (5,6-Dimethylpyridin-2-yl)methanol

Participants

Reaction Steps

Diisobutyl aluminum hydride (4.45 mL, 25 mmol) was added to the carbomethoxypyridine from Step 3 (1.4 g, 8.4 mmol ) in THF (40 mL) at -78° C. The mixture was stirred overnight with slow warming to +4° C. The reaction was quenched with solid tartaric acid followed by aqueous sodium potassium tartrate and stirred 1/2 hour. Neutralization with saturated aq. NaHCO3 and extraction with EtOAc (3×) gave after treatment with brine and evaporation 1.12 g (97%) of the title compound.

Provenance & Evidence