Acetonitrile → HCID 86223453, compound

Temperature

-78 °C

Acetonitrile (11.5 mL, 219 mmol) in THF (300 mL) was cooled to −78° C. and n-BuLi (2.5 M in hexanes, 96 mL) was added slowly. The mixture was stirred at −78° C. for 2 h. 3-Methyl-2-butenal (25 mL, 262 mmol) dissolved in dry THF (50 mL) was added slowly and after 15 min the reaction was quenched with HCl (3N, 175 mL). After evaporation of the majority of solvents, the residue was extracted twice with diethylether. The combined ether extracts were dried (sodium sulfate), filtered and concentrated to give crude 3-hydroxy-5-methyl-hex-4-enenitrile (29.6 g, 100%) as a yellow oil.

1. additionwas added slowly and after 15 min the reaction
2. customwas quenched with HCl (3N, 175 mL)
3. customAfter evaporation of the majority of solvents
4. extractionthe residue was extracted twice with diethylether
5. dry with materialThe combined ether extracts were dried (sodium sulfate)
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-ed5c90f87a9c434bbf4e48a114373af8

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07973082B2