Tetrabutylammonium Fluoride → 4-(Hydroxymethyl)-6-methylpicolinonitrile

HRID 426247Notes

Reaction equation

HRID 426247 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([C:15]#[N:16])[CH:9]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:6][CH2:7][C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([C:15]#[N:16])[CH:9]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 1317294314-(Tert-butyl-dimethyl-silanyloxymethyl)-6-methyl-pyridine-2-carbonitrile

Product 1

HCID 591848654-(Hydroxymethyl)-6-methylpicolinonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-pyridine-2-carbonitrile (8 g, 30.53 mmol) was stirred with 1M tetrabutylammonium fluoride in THF (32 ml, 32 mmol) in THF (30 ml) at room temperature. After 1 hr., the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (4:1)) to afford 4.07 g (90%) of 4-Hydroxymethyl-6-methyl-pyridine-2-carbonitrile as a white solid. m.p. 136-138° C.; 1H NMR (200 MHz, CDCl3) δ 2.59 (3H, s), 4.78 (2H, s), 7.39 (1H, s), 7.53 (1H, s).

Workup

  1. custom, the mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent, ether:hexane (4:1))

Sources & evidence

ORD record
ord-8d22b6965cb047d8884eca338f92f15a
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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