Water → (4-Phenylbicyclo[2.2.2]oct-1-yl)acetonitrile

HRID 908128Notes

Reaction equation

HRID 908128 reaction equation
C1(C)C=CC(S(O[CH2:11][C:12]23[CH2:19][CH2:18][C:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)([CH2:16][CH2:17]2)[CH2:14][CH2:13]3)(=O)=O)=CC=1.[C-:27]#[N:28].[Na+].O>CS(C)=O>[C:20]1([C:15]23[CH2:18][CH2:19][C:12]([CH2:11][C:27]#[N:28])([CH2:17][CH2:16]2)[CH2:13][CH2:14]3)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 866252464-Phenylbicyclo[2.2.2]oct-1-ylmethyl toluene-4-sulfonate

Product 1

HCID 67414049(4-Phenylbicyclo[2.2.2]oct-1-yl)acetonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 4-phenylbicyclo[2.2.2]oct-1-ylmethyl toluene-4-sulfonate (2.5 g, 6.75 mmol) and sodium cyanide (0.5 g, 10.20 mmol) in DMSO (20 mL) was heated at 100° C. under nitrogen for 5 h. After cooling overnight the mixture was poured into water (100 mL) then extracted with DCM (2×100 mL) then methyl t-butyl ether (3×100 mL). The DCM and methyl t-butyl ether phases were separately combined, washed with water (50 mL) and dried (MgSO4). The organic phases were then combined and the solvents evaporated to give the crude product which was purified by silica column chromatography (silica 40-63 micron) eluting with hexane:ethyl acetate 19:1 to give the title compound as a white solid (1.4 g; 93%).

Workup

  1. temperatureAfter cooling overnight the mixture
  2. extractionthen extracted with DCM (2×100 mL)
  3. washwashed with water (50 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvents evaporated
  6. customto give the crude product which
  7. customwas purified by silica column chromatography (silica 40-63 micron)
  8. washeluting with hexane:ethyl acetate 19:1

Sources & evidence

ORD record
ord-3aa235caef6c4e2b91ffd27c9033d432
Source dataset
uspto-grants-2011_09
Patent number
US08017603B2

Reaction notes

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