Isobutyronitrile → HCID 19083223, compound

To a solution of 13.8 g(0.2 mol) of isobutyronitrile dissolved in 50 ml of absolute tetrahydrofuran(THF) was added 2.0M solution of benzyl magnesium chloride(110 ml, 0.22 mol) at room temperature. The reaction mixture was refluxed for 1 hour and then cooled to room temperature. 200 ml of methanol and 11.4 g(0.3 mol) of NaBH4 were added to the resulting solution and the whole mixture was stirred at room temperature for 1 hour. The reaction was quenched by adding 300 ml of 1N hydrochloric acid and the solvent was removed by distillation under a reduced pressure. The reaction mixture was adjusted to pH 11 with 1N NaOH solution, extracted with chloroform, dried over anhydrous Na2SO4, and 50 ml of 5N hydrochloric acid in methanol was added thereto. The resulting solution was purified by column chromatography using dichloromethane: methanol(10:1) as an eluent to give 37.5 g of the title compound(yield:94%).

1. temperatureThe reaction mixture was refluxed for 1 hour
2. customThe reaction was quenched
3. additionby adding 300 ml of 1N hydrochloric acid
4. customthe solvent was removed by distillation under a reduced pressure
5. extractionextracted with chloroform
6. dry with materialdried over anhydrous Na2SO4, and 50 ml of 5N hydrochloric acid in methanol
7. additionwas added
8. customThe resulting solution was purified by column chromatography

ORD record

ord-992c18a04a064096acd8ce7d89de0b80

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05763631