3-Hydroxybenzaldehyde → HCID 18930704, compound

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).

1. customthe solvent was evaporated under vacuum
2. additionThe mixture was diluted with EtOAc (300 mL)
3. extractionextracted with 1M NaOH (20 mL), water (2×20 mL), and brine (10 mL)
4. customAfter drying
5. custom(MgSO4), and evaporation
6. customthe product was purified by chromatography on silica gel
7. washeluting with 0% to 50% EtOAc in hexane
8. customEvaporation of solvent

ORD record

ord-11f9f5ce952341a9b001d0cab1c509ab

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05739163