Hydrochloric Acid → 5-Methoxy-4,4-dimethyl-3-oxopentanenitrile

HRID 469758Notes

Reaction equation

HRID 469758 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=O)[C:6]([CH3:11])([CH3:10])[CH2:7][O:8]C.[C:13](#[N:15])[CH3:14].Cl>C1(C)C=CC=CC=1>[CH3:3][O:4][CH2:5][C:6]([CH3:11])([CH3:10])[C:7](=[O:8])[CH2:14][C:13]#[N:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 24758Sodium hydride2×HCID 14302192Methyl 3-methoxy-2,2-dimethylpropanoate

Product 1

HCID 108989285-Methoxy-4,4-dimethyl-3-oxopentanenitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

60% sodium hydride in mineral oil (667.2 mg, 16.68 mmol) in toluene (15 mL) is heated to reflux. A solution of 3-methoxy-2,2-dimethyl-propionic acid methyl ester (1.742 g, 11.916 mmol) and acetonitrile (0.878 mL, 16.68 mmol) in toluene (5 mL) is added dropwise through an additional funnel into the NaH suspension in toluene. After the addition, the reaction is stirred at reflux for 3 hours. After cooling, the reaction mixture is neutralized to PH˜7 by adding 1N HCl aqueous solution. The mixture is extracted with ethyl acetate 3 times. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound.

Workup

  1. additionAfter the addition
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. extractionThe mixture is extracted with ethyl acetate 3 times
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d614fa2da10243d684cd0f6ca42c72bd
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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