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

HRID 74860

반응식

HRID 74860 반응식
[CH2:1](O)[CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[CH:16]([CH2:17]CC[CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[OH-].[K+].[C:31](#[N:34])[CH:32]=[CH2:33].C1[O:52][CH2:51][CH2:50]OCCOCCOCCOCCOC1>C(Cl)Cl>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[CH:16]([CH2:17][CH:51]([O:52][CH2:33][CH2:32][C:31]#[N:34])[CH2:50][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

참가 물질

6

반응물 4

HCID 7855AcrylonitrileHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 66603436(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

생성물 1

HCID 674348303-(Cholestan-3-yloxy)propanenitrile수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  1. washThe organic layer was washed with brine
  2. dry with materialdried (Na2SO4) before the solvent
  3. customwas evaporated
  4. customThe residue was recrystallized from hot MeOH

출처 및 근거

ORD 기록
ord-acd60867f8ae432c9d1b12de2d0c0c94
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828952B2

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