3-Hydroxybenzaldehyde → HCID 18930704, compound

Participants

Reaction Steps

Diisopropylazodicarboxylate (2.0 mL, 10 mmol) was added to a solution of 3-hydroxybenzaldehyde (1.23 g, 10 mmol), 2-(t-butyloxycarbonylamino) ethanol (1.6 g, 10 mmol), and triphenylphosphine 2.7 g, 10 mmol) with stirring in dry THF (50 mL) in an ice bath. After allowing the reaction mixture to warm to room temperature overnight, the solvent was evaporated under vacuum. The mixture was diluted with EtOAc (300 mL) and extracted with 1M NaOH (20 mL), water (2×20 mL), and brine (10 mL). After drying (MgSO4), and evaporation, the product was purified by chromatography on silica gel, eluting with 0% to 50% EtOAc in hexane. Evaporation of solvent yielded a pale yellow viscous oil (1.6 g), which was only about 80% pure. 1H NMR(300 MHz, CDCl3): major component 9.97 (s, 1H), 7.48-7.13 (m, 4H), 4.97 (br, 1H), 4.09-4.05 (m, 2H), 3.58-3.53 (m, 2H), 1.45 (s, 9H). IR(neat): cm-1 3353 (s, br), 1694 (s). MS(NH3): 283 (base, M+NH4).

Provenance & Evidence