4-Chlorophenol → HCID 53721700, compound

[2-(2-Hydroxy-ethoxy)-ethyl]-carbamic acid benzyl ester (2.39 g, 10 mmol), 4-chlorophenol (1.29 g, 10 mmol), and triphenylphosphine (2.89 g, 11 mmol) were dissolved in tetrahydrofuran (50 ml), followed by the dropwise addition of diethylazodicarboxylate (1.73 ml, 11 mmol). After the addition, the reaction solution was stirred at room temperature for 10-12 hours. The solvent was then removed in vacuo. The remaining residue was stirred in 30% EtOAc in hexane (200 mL) for 10 minutes and a white solid was formed. This solid was then filtered and washed with 30% EtOAc in hexane (3×20 mL). The filtrates were combined and the solvents were removed in vacuo. The remaining residue was purified by flash column chromatography (SiO2, 2:1 hexane:EtOAc) to give {2-[2-(4-chloro-phenoxy)-ethoxy]-ethyl}-carbamic acid benzyl ester as clear solid (3.49 g, 99.8% yield). 1H-NMR (CDCl3, ppm) 7.35 (m, 5H), 7.20 (d, 2H), 6.82 (d, 2H), 5.22 (b, 1H), 5.10 (s, 2H), 4.07 (t, 2H), 3.80 (t, 2H), 3.62 (t, 2H), 3.41 (q, 2H). ESMS 350.1 (M+l), 372.1 (M+23).

1. additionAfter the addition
2. customThe solvent was then removed in vacuo
3. stirringThe remaining residue was stirred in 30% EtOAc in hexane (200 mL) for 10 minutes
4. customa white solid was formed
5. filtrationThis solid was then filtered
6. washwashed with 30% EtOAc in hexane (3×20 mL)
7. customthe solvents were removed in vacuo
8. customThe remaining residue was purified by flash column chromatography (SiO2, 2:1 hexane:EtOAc)

ORD record

ord-1ada3b87eb2c4f33b97d361299f1e628

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06255323B1