Isopropanol → 6-(Iso-propoxy)methyl-pyridine-3-carbonitrile

HRID 1190973Notes

Reaction equation

HRID 1190973 reaction equation
[CH:1]([OH:4])([CH3:3])[CH3:2].[OH-].[K+].Br[CH2:8][C:9]1[N:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1>O.S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]([O:4][CH2:8][C:9]1[N:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 219277766-(Bromomethyl)pyridine-3-carbonitrile

Product 1

HCID 584956066-(Iso-propoxy)methyl-pyridine-3-carbonitrileYield 45%

Reagents, catalysts & solvents 2

HCID 11433187Bis(tetrabutylammonium) sulphateCatalystHCID 962WaterSolvent

Procedure

Add iso-propanol (2.2 g, 25 mmol) and tetrabutylammonium sulfate (28 mg, 0.08 mmol) to a solution of potassium hydroxide (7.1 g, 127 mmol) in water (7 mL) and stir at room temperature for 15 min. Add 6-bromomethyl-pyridine-3-carbonitrile (1 g, 5.08 mmol) and stir the mixture for 24 h at room temperature. Add water (15 mL) and extract with DCM (15 mL). Filter through an IST® phase separator frit to separate the organic phase and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 1:1 gradient) to obtain the desired intermediate as a crystalline solid (0.4 g, 45%). MS (ES+) m/z: 177 (M+H)+.

Workup

  1. extractionAdd water (15 mL) and extract with DCM (15 mL)
  2. filtrationFilter through an IST® phase separator frit
  3. customto separate the organic phase
  4. concentrationconcentrate in vacuo
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 1:1 gradient)

Sources & evidence

ORD record
ord-2ac6a0d756ee4c6e849cedd7d7df0b36
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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