Acetonitrile → 5-Hydroxy-4,4-dimethyl-3-oxopentanenitrile

HRID 220214Notes

Reaction equation

HRID 220214 reaction equation
[Si]([O:8][CH2:9][C:10]([CH3:16])([CH3:15])[C:11]([O:13]C)=O)(C(C)(C)C)(C)C.[H-].[Na+].[C:19](#[N:21])[CH3:20]>C1(C)C=CC=CC=1>[OH:8][CH2:9][C:10]([CH3:15])([CH3:16])[C:11](=[O:13])[CH2:20][C:19]#[N:21]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 12044793Methyl 3-(tert-butyldimethylsilyloxy)-2,2-dimethylpropanoate

Product 1

HCID 120447945-Hydroxy-4,4-dimethyl-3-oxopentanenitrileYield 88.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 3-(tert-butyldimethylsilyloxy)-2,2-dimethylpropanoate (0.63 g, 2.557 mmol) was added to toluene and NaH (0.4090 g, 10.23 mmol) and acetonitrile (0.534 mL, 10.23 mmol) and stirred overnight in a sealed vessel for 6 hours at 90° C. The solids were removed by filtration and rinsed with toluene. The toluene filtrate was concentrated, and the resulting solids were added to 3 N HCl, stirred for 30 minutes and then washed with ether. The mixture was concentrated and the resulting solids were rinsed several times with DCM. The DCM was dried over MgSO4, filtered and evaporated to provide the title compound as an oil (320 mg), which was used directly in the next step.

Workup

  1. customThe solids were removed by filtration
  2. washrinsed with toluene
  3. concentrationThe toluene filtrate was concentrated
  4. additionthe resulting solids were added to 3 N HCl
  5. stirringstirred for 30 minutes
  6. washwashed with ether
  7. concentrationThe mixture was concentrated
  8. washthe resulting solids were rinsed several times with DCM
  9. dry with materialThe DCM was dried over MgSO4
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-9186ebb079aa45df8186689a56e081cc
Source dataset
uspto-grants-2012_06
Patent number
US08202899B2

Reaction notes

Loading…