Acrylonitrile → 3-(Cholestan-3-yloxy)propanenitrile

Participants

Role	Name	HCID	Charge
Reactant	Acrylonitrile	HCID 7855	—
Reactant	Potassium Hydroxide	HCID 14797	—
Reactant	18-Crown-6	HCID 28557	—
Reactant	(6R)-6-[(8R,9S,10S,13R,14S,17R)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptan-1-ol	HCID 66603436	—
Solvent	Dichloromethane	HCID 6344	—
Product	3-(Cholestan-3-yloxy)propanenitrile	HCID 67434830	80%

Reaction Steps

Cholestanol (1.554 g, 3.998 mmol) was dissolved in DCM (6 mL). To this solution was added KOH (40% w/w in water, 1.2 mL) and acrylonitrile (0.8 mL), followed by 18-crown-6 (104 mg). The mixture was stirred at room temperature overnight. The organic layer was washed with brine and dried (Na2SO4) before the solvent was evaporated. The residue was recrystallized from hot MeOH to yield the pure product as a colourless crystalline solid (1.42 g, 80% yield). 1H NMR (400 MHz, CDCl3) δ: 3.68 (t, 2H, CH2O), 3.29 (m, 1H, CHO), 2.57 (t, 2H, CH2CN), 1.98-0.58 (m, 31H), 0.89 (d, 3H, J=6.6, CH3), 0.87 (d, 3H, J=1.8, CH3), 0.85 (d, 3H, J=2.0, CH3), 0.79 (s, 3H, CH3), 0.64 (s, 3H, CH3).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08828952B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-acd60867f8ae432c9d1b12de2d0c0c94
Source note	uspto-grants-2014_09