Dimethyl Sulfoxide → HCID 21392721, compound

HRID 461992Notes

Reaction equation

HRID 461992 reaction equation
S(O[CH2:12][C:13]12[CH2:20][CH2:19][C:16]([CH3:21])([CH2:17][CH2:18]1)[CH2:15][CH2:14]2)(C1C=CC(C)=CC=1)(=O)=O.[C-:22]#[N:23].[Na+].CS(C)=O>C(Cl)Cl>[CH3:21][C:16]12[CH2:15][CH2:14][C:13]([CH2:12][C:22]#[N:23])([CH2:18][CH2:17]1)[CH2:20][CH2:19]2

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 13409934HCID 13409934, compound

Product 1

HCID 21392721HCID 21392721, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture containing 0.065 mole of 4-methylbicyclo[2.2.2]oct-1-yl methanol tosylate, 0.1 mole of sodium cyanide, and 100 ml. of dimethyl sulfoxide is stirred at 70° C for 4 hours and then poured into 500 ml. of methylene chloride. The organic phase is then washed four times with water, separated and dried with anhydrous magnesium sulfate and filtered. The filtrate is then evaporated under vacuum affording an oil which is then chromatographed on silica gel eluting with 10% ethyl acetate-90%, vol., hexane affording 4-methylbicyclo[2.2.2]oct-1-yl acetonitrile.

Workup

  1. additionpoured into 500 ml
  2. washThe organic phase is then washed four times with water
  3. customseparated
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate is then evaporated under vacuum
  7. customaffording an oil which
  8. customis then chromatographed on silica gel eluting with 10% ethyl acetate-90%, vol., hexane

Sources & evidence

ORD record
ord-a5b825c35c3b4e0cb867ed122f472847
Source dataset
uspto-grants-1977_12
Patent number
US04064258

Reaction notes

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