Tetrahydrofuran → HCID 66619387, compound

Participants

Reaction Conditions

Reaction Steps

To an ice-cold solution of 0.5 g (2.5 mmol) 6-benzyloxy-3-hydroxypyridine (commercially available) in 5 mL tetrahydrofuran, 0.12 g (2.7 mmol) sodium hydride (55% dispersion in mineral oil) was added portion wise. After vigorous gas evolution had ceased, the reaction mixture was stirred for another 20 min. at 0° C. and then 0.44 mL (3.1 mmol) 2,4-dibromobutyrate (commercially available) were added dropwise. The light brown suspension was stirred for 23 h at room temperature and then poured onto water. The aqueous phase was extracted three times with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulfate and filtered. To the filtrate silica gel was added and the slurry evaporated. The resulting solid was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 70:30) to give the product as a colorless oil (59%). MS (Turbo Spray): m/z=382.1 [M+H].

Provenance & Evidence