Isopropanol → HCID 53641585, compound

Participants

Reaction Conditions

Reaction Steps

A solution of isopropanol (2.9 ml, 0.038 mole) and triethylamine (5.3 ml, 0.038 mole) in 50 ml. of ether was added to a solution of ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (13.2 g, 0.04 mole) in 150 ml. of ether at 0° C. After three hours, the solution was filtered and the cooled (0° C.) filtrate was treated with a solution of thiophenol (3.9 ml, 0.038 mole) and triethylamine (5.3 ml, 0.038 mole) in 50 ml. of ether. The resulting mixture was stirred at 25° C. for 16 hours, then filtered. The filtrate was washed with 3% hydrochloric acid, 3% ammonium hydroxide and saturated sodium chloride solution, then concentrated in vacuo. The residual oil was chromatographed on silica gel eluting with ethyl acetate/cyclohexane (6:4) to afford ethyl N-trifluoroacetyl-N-(isopropoxy(phenylthio)phosphonomethyl)glycinate (7.7 g) as a light yellow oil, ND25 =1.4951.

Provenance & Evidence