Water → HCID 67299906, compound

HRID 2368215Notes

Reaction equation

HRID 2368215 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-f4e229691fa544a5ab67d8582dc3f899
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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