Hydracrylonitrile → HCID 19982452, compound

Participants

Reaction Steps

Diisopropylmethyl phosphoramidite chloride (10.7 g, 52.5 mmol) was added to a magnetically stirred solution of THF (100 ml), diisopropylethylamine (27.5 ml, 157.5 mmol) and 3-hydroxypropionitrile (7.2 ml, 105 mmol) at 0° C. After 4 hours, the mixture was warmed to room temperature and stirred for an additional 2 hours. The hydrochloride salt was removed from the reaction mixture by filtration through a scintered glass funnel. The resulting filtrate was recovered, diluted 1/1 with ethyl acetate, and washed with three 100 ml portions of 5% NaHCO3. The organic portion was then dried over Na2SO4 and evaporated to yield the crude product which was dissolved in a mixture of dichloromethane/hexane/triethylamine (6/4/1 v/v/v) (50 ml) and applied to a column of silica gel (175 g) which had been equilibrated with the same solvent mixture. The column was eluted with the solvent mixture and fractions (20 ml) were collected. Fractions which contained the desired product were identified as 2-cyanoethoxymethoxy-N,N-diisopropylaminophosphine (hereinafter referred to as Compound III) represented by the formula set forth below: ##STR6## wherein i-Pr is isopropyl. Fractions containing Compound III were pooled, evaporated, and then coevaporated with toluene (3×5 ml).

Provenance & Evidence