Acetonitrile → HCID 59570361, compound

HRID 1880768Notes

Reaction equation

HRID 1880768 reaction equation
[C:1](#[N:3])C.[F:4][C:5]([F:20])([F:19])[C:6]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)([CH3:12])[O:7][Si:8]([CH3:11])([CH3:10])[CH3:9].C[Si](C#N)(C)C>C(N(CC)CC)C>[F:20][C:5]([F:19])([F:4])[C:6]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:1]#[N:3])[CH:14]=1)([CH3:12])[O:7][Si:8]([CH3:9])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 82115Trimethylsilyl cyanideHCID 59570279HCID 59570279, compound

Product 1

HCID 59570361HCID 59570361, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

To 30 ml of acetonitrile were added 4 g of 4-[2,2,2-trifluoro-1-methyl-1-(trimethylsilyloxy)ethyl]pyridine=N-oxide, 4.45 ml of triethylamine, and 4.75 g of trimethylsilyl cyanide, and the mixture was stirred at 90° C. for 20 hours. Thereafter, the reaction solution was allowed to cool to room temperature, and concentrated. The residue was subjected to silica gel column chromatography to obtain 4.3 g of 4-[2,2,2-trifluoro-1-methyl-1-(trimethylsilyloxy)ethyl]pyridine-2-carbonitrile.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-80a6dab7fbe94044ae3bd915d9f9cd53
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

Loading…