3-Hydroxybenzaldehyde → tert-Butyl 4-(3-formylphenoxy)piperidine-1-carboxylate

Participants

Reaction Steps

To a mixture of 3-hydroxybenzaldehyde (1.0 g), tert-butyl 4-hydroxypiperidine-1-carboxylate (1.67 g, 1.1 eq), triphenylphosphine (2.35 g, 1.1 eq) in THF (15 mL) at 0° C. was added dropwise DEAD (6.74 g, 4.75 eq). The mixture was warmed to room temperature and stirred for 2 days. To the reaction mixture was added saturated NaHCO3 (aq), and the aqueous layer was extracted with ethyl acetate (15 mL×3), the organic layers were combined, dried (Na2SO4), and purified on silica gel column chromatography (10% ethyl acetate in pentane) to obtain the desired product as a light yellow oil (900 mg, 38% yield).

Provenance & Evidence