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

関与物質

役割	名称	HCID	仕込み量
反応物	Acrylonitrile	HCID 7855	—
反応物	Potassium Hydroxide	HCID 14797	—
反応物	18-Crown-6	HCID 28557	—
反応物	(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	—
溶媒	Dichloromethane	HCID 6344	—
生成物	3-(Cholestan-3-yloxy)propanenitrile	HCID 67434830	80%

反応手順

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).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08828952B2
出典データセット	uspto-grants-2014_09
ORD ID	ord-acd60867f8ae432c9d1b12de2d0c0c94
出典メモ	uspto-grants-2014_09