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

HRID 74860

Reaction equation

HRID 74860 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-acd60867f8ae432c9d1b12de2d0c0c94
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Linked notes

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