Diethyl Ether → HCID 9995583, compound

Participants

Reaction Steps

1-Cyclohexyl-1-hydroxy-1-phenyl-2-propanone (2.83 g, 12.2 mmole) was added to 50 mL of dry tetrahydrofuran (THF). The solution was stirred and a solution of pyrrolidone hydrotribromide (6.08 g, 12.3 mmole) in 125 mL of dry THF was added dropwise over a period of 2 hours. After being refluxed for 4 hours, the reaction mixture was cooled. Ether was added and the solution washed twice with water and dried over magnesium sulfate. Upon evaporation of the solution to dryness, an orange oil was isolated. The product was purified by flash column chromatography (silica, hexane/ethyl acetate (99:1 followed by 95:5) to afford 3-bromo-1-hydroxy-1-cyclohexyl-1-phenyl-2-propanone (1 44 g, 37.7%). NMR (CDCl3) 1.0-2.0 (m, 10 H), 2.4 (m, 1 H), 3.5 (s, 1 H), 4.1 (s, 1 H), 7.2-7.6 (m, 5 H).

Provenance & Evidence