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

참여 물질

역할	이름	HCID	투입량
반응물	Acrylonitrile	HCID 7855	—
반응물	Potassium Hydroxide	HCID 14797	—
반응물	18-Crown-6	HCID 28557	—
반응물	(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	—
용매	Dichloromethane	HCID 6344	—
생성물	3-(Cholestan-3-yloxy)propanenitrile	HCID 67434830	80%

반응 단계

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).

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08828952B2
출처 데이터셋	uspto-grants-2014_09
ORD ID	ord-acd60867f8ae432c9d1b12de2d0c0c94
출처 메모	uspto-grants-2014_09