Water → HCID 67299906, compound

HRID 467618Notes

Reaction equation

HRID 467618 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][O:10][CH3:11])=[N+:6]([O-])[CH:7]=1.[CH2:12]([N:14](CC)CC)C.C[Si](C#N)(C)C.O>C(#N)C>[Br:1][C:2]1[C:7]([C:12]#[N:14])=[N:6][C:5]([CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 67299910HCID 67299910, compound

Product 1

HCID 67299906HCID 67299906, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 5-bromo-2-methoxymethyl-pyridine-1-oxide (5.0 g, 22.7 mmol), triethylamine (12.7 ml, 91 mmol) and trimethylsilyl cyanide (9.1 ml, 68.2 mmol) in acetonitrile (10 ml) was heated in a sealed tube to 120° C. for 18 hours. After completion of the reaction, water was added to the reaction mixture and acetonitrile was removed. The crude material was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried, filtered, and evaporated. The crude product was purified by silica gel chromatography using an ethyl acetate/hexane eluent to yield 3.0 g (58%) of the title compound.

Workup

  1. customwas removed
  2. extractionThe crude material was extracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c4152d288f934e238b87bab0de3af629
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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