Water → 1344144-96-2

HRID 869175Notes

Reaction equation

HRID 869175 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-fd93d143c2b64efa85aa65cd0f51c2c8
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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