Propofol → (+/-)-[2,6-Bis(1-methylethyl)phenyl]nonyl Phosphoryl Chloride

Participants

Reaction Steps

To a solution of phosphorus oxychloride (1.53 g, 10.0 mmol) and triethylamine (3.5 mL, 25.0 mmol) in toluene (20 mL) at 0° C. is added dropwise a solution of 2,6 diisopropylphenol (1.78 g, 10.0 mmol) in toluene (5 mL). The mixture is allowed to warm slowly to room temperature and stirred for 2 hours. The mixture is cooled to 0° C., and a solution of 1-nonanol (1.44 g, 10.0 mmol) in toluene (5 mL) is added dropwise. The mixture is allowed to warm to room temperature and stirred for 2 hours. The mixture is filtered and the filtrate concentrated to afford 4.1 g of a crude oil, which is taken up in 1:1 EtOAc/hexane and filtered through a small pad of silica gel. The filtrate is concentrated to afford 3.7 g of a light yellow liquid; 1H NMR (200 MHz, CDCl3)δ7.17 (br s, 3 H), 4.30-4.10 (m, 2 H), 3.43 (m, 2 H), 1.85-1.65 (m, 4 H), 1.45-1.10 (m, 10 H), 1.25 (d, J=7 Hz, 12 H), 0.89 (t, J=7 Hz, 3 H).

Provenance & Evidence