2-Bromopropane → HCID 19428133, compound

Participants

Reaction Steps

67 g (268 mmol) of 6-hydroxy-3-(2-hydroxyethyl)-7-methoxy-4-methyl-2H-1-benzopyran-2-one (Example 41) is carefully added, using an ice bath for cooling, to 11.8 g (295 mmol) of sodium hydride (60% in white oil) in 300 ml of DMF. The mixture is stirred for 1 hour at room temperature, and then 49.5 g (402 mmol) of 2-bromopropane is added dropwise and the mixture is stirred for 24 hours at 60° C. under nitrogen. After adding a further 3.33 g (83 mmol) of sodium hydride and 52.4 g (426 mmol) of 2-bromopropane, the mixture is stirred for a further 24 hours at 60° C. The solution is evaporated, extracted with ethyl acetate, and the organic phase is washed with water, dried with Na2SO4 and re-evaporated. The product is purified by column chromatography over silica gel 60 (eluent: ethyl acetate). Yield 53.3 g (68%); m.p. 110°-112° C. (from acetone/PE).

Provenance & Evidence