Hydracrylonitrile → HCID 19982451, compound

Participants

Reaction Steps

Diisopropylamino phosphorodichloridite (made in accordance with the procedure set forth in Takeo, Shimidzu, et al. Nucleic Acid Research Symposium Series No. 12,55-58 (1983)) (14.2g, 70.0 mmol) was added to a magnetically stirred solution of tetrahydrofuran (100 ml), diisopropylethylamine (36.6 ml, 210 mmol) and 3-hydroxypropionitrile (9.6 ml, 140 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 Na and evaporated to yield 17.7g of crude product as a yellow oil. The oil 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 bis-(2-cyanoethoxy)-N,N-diisopropylaminomethoxyphosphine (hereinafter referred to as Compound II) represented by formula set forth below: ##STR5## wherein i-Pr is isopropyl. (Rf=0.60 silica gel TLC developed in ethyl acetate/triethylamine 9/1). Fractions containing Component II were pooled, evaporated, and then coevaporated with toluene (3×5 ml) to yield the desired product as a colorless oil (11.1 g, 58.7%)31 p NMR=-146.75 ppm, relative to trimethylphosphate in CH2Cl2.

Provenance & Evidence