Dichloromethane → HCID 23311355, compound

Participants

Reaction Steps

A solution of 28.6 g (102 mmole) 2-(2-oxo-3-phenyl-3-dihydrobenzofuranyl)-N,N-dimethylethylamine in 300 ml anhydrous Et2O was added to 7.74 g (204 mmole) LiAlH4 in 150 ml Et2O at ice bath temperature and this mixture stirred at that temperature for 30 minutes. After further stirring for 2 hours at room temperature, the reaction mixture was quenched with saturated Na2SO4, filtered, and the solids washed with excess EtOAc (4×350 ml). The combined organics were washed with saturated Na2CO3 (300 ml) and saturated NaCl (200 ml), and dried over Na2SO4. Filtration and evaporation gave 28 g of a crude oil which solidified on standing. A solution of 5 g of this material in a minimum amount of CH2Cl2 was added to excess Et2O/HCl. Filtration of the precipitated salt gave 5.5 g of a solid which was recrystallized from EtOH to give 3.2 g (57%) of crystals, m.p. 199°-201°.

Provenance & Evidence