3-(2-(Trimethylsilyl)ethoxy)isonicotinonitrile → 3-Hydroxypyridine-4-carbonitrile

HRID 911088Notes

Reaction equation

HRID 911088 reaction equation
C[Si](C)(C)CC[O:5][C:6]1[CH:13]=[N:12][CH:11]=[CH:10][C:7]=1[C:8]#[N:9].[F-].C([N+](CCCC)(CCC)CCCC)CCC>C1COCC1>[OH:5][C:6]1[CH:13]=[N:12][CH:11]=[CH:10][C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 666177473-(2-(Trimethylsilyl)ethoxy)isonicotinonitrileHCID 86634790N,N-dibutyl-N-propylbutan-1-aminium fluoride

Product 1

HCID 129590773-Hydroxypyridine-4-carbonitrileYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A flask was charged with 3-(2-(trimethylsilyl)ethoxy)isonicotinonitrile (1.30 g, 5.90 mmol), THF (5 mL) and N,N-dibutyl-N-propylbutan-1-aminium fluoride (11.8 ml, 11.8 mmol) in THF was added. The reaction mixture was stirred at ambient temperature for 1 hour and then concentrated. The crude product was purified by silica gel chromatography, eluting with DCM and 5% methanol in DCM to give the desired product (0.7 g, 99% yield) as dark brown oil.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. customThe crude product was purified by silica gel chromatography
  4. washeluting with DCM and 5% methanol in DCM

Sources & evidence

ORD record
ord-6cf341eb2e5d4db39542c56207d07b28
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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