Water → 1344144-96-2

HRID 2276774Notes

Reaction equation

HRID 2276774 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 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(6-methoxypyridin-2-yl)cyclobutanecarbonitrile (1.7 g, 8.8 mmol) in THF (20 mL) was added lithium aluminum hydride solution (1.0 M in THF, 11 mL, 11 mmol). The mixture was refluxed for 1.5 h and allowed to cool to room temperature. Water (0.43 mL) was slowly added, followed by 0.43 mL of 3 M NaOH, and then three additions of 0.43 mL of water. 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) as a viscous oil.

Workup

  1. temperatureThe mixture was refluxed for 1.5 h
  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-49f2b9dd125a49f788ecd92eb7bce5d3
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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