Ammonia → HCID 17982946, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl pyridine (1.20 g) in anhydrous THF (15 ml) under nitrogen and at −78° C. was added LDA (3.22 ml), and the solution stirred at −78° C. for 1 hour. 3,5 dibenzyloxy-benzaldehyde (2.05 g) was then added dropwise as a solution in THF, and the reaction mixture allowed to warm to ambient temperature over 1 hour. Water (20 ml) was added and the resulting mixture extracted with ethyl acetate (3×30 ml). The extracts were combined, washed with brine (20 ml), dried (MgSO4) and evaporated to give a gum. This was dissolved in THF (10 ml) and concentrated hydrochloric acid (10 ml) added. The mixture was stirred at ambient temperature for 3 hours, cooled to 0° C. and taken to pH 8.5 with concentrated ammonia solution. The mixture was diluted with water (50 ml) and extracted with ethyl acetate (3×100 ml). The extracts were combined, dried (MgSO4) and evaporated to leave an oil which was purified by MPLC on silica, eluting with 60–100% ethyl acetate in hexane to give 6-{2-[3,5-bis(benzyloxy)phenyl]-2-hydroxyethyl}pyridin-3-ol (2.25 g) as a glass, m/z 428 (M+H)+.

Provenance & Evidence