Acetonitrile → HCID 54006069, compound

A solution of aluminum chloride (1.44 g, 10.8 mmol) in tetrahydrofuran (25 ml) was added carefully to lithium aluminum hydride (1.23 g, 32.4 mmol) in tetrahydrofuran (25 ml), and the mixture stirred at room temperature for 10 mins. A solution of the intermediate acetonitrile in tetrahydrofuran (50 ml) was then added and the reaction stirred at room temperature for 3 hrs. The reaction was quenched by the addition of hydrochloric acid, then basified using aqueous NaOH solution. The mixture was extracted with ethyl acetate, the combined organic extracts dried over MgSO4 and evaporated under reduced pressure. The crude product was redissolved in ethyl acetate, extracted into citric acid, and these aqueous extracts rebasified using aqueous NaHCO3 solution. This was then re-extracted with ethyl acetate, and the combined extracts evaporated under reduced pressure to provide the title compound as a yellow oil, (1.79 g, 47%).

1. stirringthe reaction stirred at room temperature for 3 hrs
2. customThe reaction was quenched by the addition of hydrochloric acid
3. extractionThe mixture was extracted with ethyl acetate
4. dry with materialthe combined organic extracts dried over MgSO4
5. customevaporated under reduced pressure
6. dissolutionThe crude product was redissolved in ethyl acetate
7. extractionextracted into citric acid
8. extractionThis was then re-extracted with ethyl acetate
9. customthe combined extracts evaporated under reduced pressure

ORD record

ord-97836944d9084509beb442220864b4f0

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06180627B2