Sodium borohydride → HCID 54511055, compound

Participants

Reaction Conditions

Reaction Steps

IX (1.65 g, 0.008 mole) was dissolved in absolute ethanol (200 ml), and the solution was cooled to 0°C. Sodium tetrahydroborate (0.70 g, 0.0185 mole) was added in one portion with stirring. The turbid solution was stirred at 0°-5°C for 15 minutes and then at room temperature for 20 hours. The solution was concentrated to 1/4 of the volume by distillation from a water bath (40°C) under reduced pressure (50 mm Hg). The residual solution was cooled to 10°C, and then cold water (800 ml) and N sodium hydroxide (25 ml) were added successively with stirring. The stirring was continued for 15 minutes at room temperature and then the pH of the emulsion was adjusted to 7.8 by addition of 3N acetic acid. The reaction mixture was extracted with two 150-ml portions of ether. The combined organic extracts were washed with water (100 ml) and dried over magnesium sulfate. The ethereal solution was evaporated to dryness from a water bath (60°C) under reduced pressure, at last under 15 mm Hg. The residual oil (1.67 g) was purified by distillation under nitrogen. 1.13 g (68%) of X were hereby obtained as a yellow liquid, b0.2 97°-99°C, nD20 1.5166.

Provenance & Evidence