Tetrahydrofuran → HCID 20313243, compound

Participants

Reaction Steps

After adding dropwise a solution of 5 g. of methyl magnesium bromide in 27 ml. of tetrahydrofuran to a mixture of 4.0 g. of 4-isopropyl-5-oxo-2-(1-oxo-5-indanyloxymethyl)morpholine and 100 ml. of tetrahydrofuran with stirring at room temperature, the mixture was stirred for 3 hours at room temperature. Then, after adding a small amount of water to the reaction mixture, the solvent was distilled off under reduced pressure. To the residue formed were added 50 ml. of ethyl acetate and 50 ml. of water to dissolve the residue and they were filtered. The ethyl acetate filtrate (100 ml.) was recovered, washed twice each with 50 ml. of saturated sodium chloride aqueous solution, and condensed under reduced pressure, the obtained residue was adsorbed on a silica gel column prepared from 100 ml. of silica gel in chloroform, and then eluted using ethyl acetate as the eluting solution. After removing the first 30 ml. of the ethyl acetate eluting solution emerging from the column, 300 ml. of the subsequent ethyl acetate eluting solution was collected and dried to provide 2.5 g. (yield 59.3%) of oily 2-(1-hydroxy-1-methyl-5-indanyloxymethyl)-4-isopropyl-5-oxomorpholine.

Provenance & Evidence