Pyridine → HCID 59609081, compound

Participants

Reaction Conditions

Reaction Steps

10.2 g (42 mmol) 2,3-dihydroxy-1,2-diphenyl-1-propanone was dissolved in 130 ml acetone. 6.6 g (84 mmol) pyridine was added and the reaction mixture was cooled to −10° C. 10.7 g (84 mmol) 3-chloropropionyl chloride was added drop wise, while the temperature was kept below 0° C. The reaction was allowed to continue for 30 minutes at 0° C., followed by 5 hours at room temperature. 150 ml ethyl acetate and 200 ml water were added to the reaction mixture. The organic fraction was isolated and the aqueous fraction was extracted for a second time with 200 ml ethyl acetate. The pooled organic fractions were dried over MgSO4 and evaporated under reduced pressure. (2,3-diphenyl-2-hydroxy-3-oxopropyl)-3-chloro-propionate was isolated by preparative column chromatography on a Prochorm LC80 column, using Kromasil Si60A 10μ and methylene chloride as eluent at a flow rate of 150 ml/min. 8 g of (2,3-diphenyl-2-hydroxy-3-oxopropyl)-3-chloro-propionate (60%) was isolated as a white crystalline product. (TLC on Merck Kieselgel 254F60, eluent methylene chloride, Rf: 0.19)

Provenance & Evidence