Water → 1344144-96-2

HRID 2276744Notes

Reaction equation

HRID 2276744 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2([C:13]#[N:14])[CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2([CH2:13][NH2:14])[CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67453617HCID 67453617, compound

Product 1

HCID 674510161344144-96-2Yield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(6-methoxypyridin-2-yl)cyclobutanecarbonitrile (1.7 g, 8.8 mmol, 1.0 equiv) in THF (20 mL) was added lithium aluminum hydride solution (1.0 M in THF, 11 mL, 11 mmol, 1.1 equiv). The mixture was refluxed for 1.5 hours and allowed to cool to room temperature. Water (0.43 mL) was added slowly followed by 0.43 mL of 3 M NaOH and then three additions of 0.43 mL of water (Fieser and Fieser workup). The resulting mixture was filtered through diatomaceous earth and rinsed with THF. The combined organics were dried over Na2SO4 and concentrated to dryness to give the desired product (1.6 g, 97%) as a viscous oil.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. filtrationThe resulting mixture was filtered through diatomaceous earth
  3. washrinsed with THF
  4. dry with materialThe combined organics were dried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2d1727cc8e1a43508e71fa29e427bb9c
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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