Tetrahydrofuran → HCID 20313234, compound

Participants

Reaction Steps

After mixing 2.5 g. of 2-(1-hydroxy-3-methyl-1-phenyl-5-indanyloxymethyl)-4-isopropyl-5-oxomorpholine, 100 ml. of tetrahydrofuran, and 1.0 g. of lithium aluminum hydride under ice-cooling, the mixture was stirred for 18 hours at room temperature and then 1 ml. of water, 1 ml. of 15% sodium hydroxide aqueous solution, and then 3 ml. of water were added to the mixture followed by stirring for 30 minutes. The mixture was then filtered and the filtrate recovered was dried under reduced pressure. The residue formed was adsorbed on a silica gel column prepared from 50 ml. of silica gel in chloroform and then eluted using ethyl acetate as the eluent. After removing the first 5 ml. of the ethyl acetate eluate emerging from the column, 150 ml. of the subsequent ethyl acetate eluate was collected and dried to provide 2.0 g. (yield 83.0%) of 2-(1-hydroxy-3-methyl-1-phenyl-5-indanyloxymethyl)-4-isopropylmorpholine.

Provenance & Evidence