Ethanol → 4-(Tert-butyl-di-methylsilyloxyethyl)-2-cyanopyridine

HRID 345341Notes

Reaction equation

HRID 345341 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][N+:14]([O-])=[CH:13][CH:12]=1)([C:4](C)(C)C)([CH3:3])C.C[Si]([C:22]#[N:23])(C)C.[CH2:24](N(CC)CC)C.C(O)C.CCC[CH2:37][CH2:38][CH3:39]>C(OCC)(=O)C>[C:38]([CH:9]([O:8][SiH:1]([CH3:3])[CH3:4])[CH2:10][C:11]1[CH:12]=[CH:13][N:14]=[C:15]([C:22]#[N:23])[CH:16]=1)([CH3:37])([CH3:39])[CH3:24]

Participants

7

Reactant 5

HCID 702EthanolHCID 8058HexaneHCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 197577894-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-1-oxo-1lambda~5~-pyridine

Product 1

HCID 1317170374-(Tert-butyl-di-methylsilyloxyethyl)-2-cyanopyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 28.6 g of 4-(tert-butyl-dimethylsilyloxyethyl)-pyridine-N-oxide, 60.3 ml of trimethylsilyl cyanide and 31.5 ml triethylamine is stirred under nitrogen at reflux for 3 hours. The dark solution is cooled in an ice bath, 30 ml of ethanol added, followed by 400 ml ethyl acetate and 200 ml hexane. The solution is washed twice with 150 ml of 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-di-methylsilyloxyethyl)-2-cyanopyridine.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureThe dark solution is cooled in an ice bath
  3. washThe solution is washed twice with 150 ml of water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-8a7c1e0864a34a6294e0af744174002e
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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