Ethanol → 4-(Tert-butyldimethylsilyloxymethyl)pyridinecarbonitrile

HRID 1587332Notes

Reaction equation

HRID 1587332 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][N+:13]([O-])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Si]([C:21]#[N:22])(C)C.C(N(CC)CC)C.C(O)C>C(OCC)(=O)C>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:21]#[N:22])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 217815154-(tert-Butyldimethylsilanyloxymethyl)pyridine 1-oxide

Product 1

HCID 145414484-(Tert-butyldimethylsilyloxymethyl)pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 37.9 g of 4-(tert-butyl-dimethylsilyloxymethyl)-pyridine-N-oxide, 84 ml of trimethylsilyl cyanide and 44 ml triethylamine is stirred under nitrogen at reflux for 21/2 hours. Dark solution is cooled in an ice bath, then 40 ml of ethanol added followed by 500 ml of ethyl acetate. The solution is washed twice with water, dried over sodium sulfate, filtered, concentrated in vacuo and purified by flash chromatography using ethyl acetate/hexane (1:10) to yield 4-(tert-butyl-dimethylsilyloxymethyl)-2-cyanopyridine.

Workup

  1. temperatureat reflux for 21/2 hours
  2. temperatureDark solution is cooled in an ice bath
  3. washThe solution is washed twice with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-5dc3991acfd249bfa50d5acddf9b1052
Source dataset
uspto-grants-1993_06
Patent number
US05217963

Reaction notes

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