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

HRID 2353085Notes

Reaction equation

HRID 2353085 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-a1b5ac102b614d878cdc120e7801dc7f
Source dataset
uspto-grants-2010_07
Patent number
US07749997B2

Reaction notes

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