Hydrochloric Acid → 2-Neopentylmalononitrile

HRID 1912897Notes

Reaction equation

HRID 1912897 reaction equation
[CH3:1][C:2]([CH3:10])([CH3:9])[CH:3]=[C:4]([C:7]#[N:8])[C:5]#[N:6].[Na+].[Cl-].[BH4-].[Na+].Cl>C(OCC)(=O)C.C(O)C>[CH2:3]([CH:4]([C:7]#[N:8])[C:5]#[N:6])[C:2]([CH3:10])([CH3:9])[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 564299Malononitrile, neopentylidene-HCID 4311764Sodium borohydride

Product 1

HCID 865936402-Neopentylmalononitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the 500 mL round bottom flask with the product from Example 10A was added 100 mL ethanol. The mixture was cooled in an ice bath (NaCl was added to the bath to keep the temperature below 0° C.) and sodium borohydride was added. The mixture was stirred for 30 minutes. 160 mL 0.5 N HCl solution was added carefully and ethyl acetate was used to extract the mixture twice. Brine was added to help the layers to separate. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude title compound was used directly in the following steps without further purification. MS (ESI) m/z 135.1 (M−H)−.

Workup

  1. additionwas added to the bath
  2. customthe temperature below 0° C.
  3. additionwas added
  4. extractionto extract the mixture twice
  5. additionBrine was added
  6. customto separate
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude title compound was used directly in the following steps without further purification

Sources & evidence

ORD record
ord-878cf42fb4284872b9c14849608957d4
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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