Water → HCID 20458963, compound

Participants

Reaction Steps

To an ice-cooled suspension of 1.56 g of lithium aluminium hydride in 200 ml tetrahydrofuran (THF) there was added 15.0 g of 8-(2-fluorobenzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester in portions so that the temperature remained below 10° C. After stirring at 0°-5° C. for an additional 1 hr., 1.6 ml water was added dropwise at 0°-10° C., followed by 1.6 ml15 % aqueous sodium hydroxide and then 4.8 ml water. The mixture was allowed to warm to room temperature with stirring, and was then suction-filtered in a sintered glass funnel. The solids left in the funnelwere thoroughly washed with 200 ml hot tetrahydrofuran and 4×150 ml hot chloroform. The filtrate and washings were combined, evaporated in vacuo, and the solid residue crystallized from acetonitrile to give the desired compound (m.p. 151°-153° C.).

Provenance & Evidence