Nitrogen → 1-[4-(Hydroxymethyl)pyridin-2-yl]ethan-1-one

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-[4-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethanone (340 mg, 1.28 mmol) in dry THF (5 mL) was treated at 0° C. with TBAF (1.9 mL of a 1M solution in THF, 1.90 mmol). The reaction mixture was stirred at 0° C. for 5 min and at rt for 1 h30. The mixture was then diluted with EA (10 mL), washed with brine (3×10 mL), dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by FC (5:1 to 1:3 hept-EA) gave the title compound as a yellow oil. TLC: rf (1:2 hept-EA)=0.10. LC-MS-conditions 02: tR=0.40 min; [M+H]+=152.24.

Provenance & Evidence