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

HRID 74860

反応式

HRID 74860 の反応式
[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]

参加物

6

反応物 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

生成物 1

HCID 674348303-(Cholestan-3-yloxy)propanenitrile収率 80%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-acd60867f8ae432c9d1b12de2d0c0c94
出典データセット
uspto-grants-2014_09
特許番号
US08828952B2

関連ノート

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