Malononitrile → HCID 59541855, compound

HRID 2388351Notes

Reaction equation

HRID 2388351 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]2)[O:3][CH2:2]1.[C:12](#[N:16])[CH2:13][C:14]#[N:15].[BH4-].[Na+]>CC(O)C>[O:3]1[C:4]2([CH2:9][CH2:8][CH:7]([CH:13]([C:12]#[N:16])[C:14]#[N:15])[CH2:6][CH2:5]2)[O:11][CH2:1][CH2:2]1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 4311764Sodium borohydride

Product 1

HCID 59541855HCID 59541855, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The title compound was prepared by the method of Dunham et al. (Synthesis 2006 (4), 680). 1,4-Cyclohexanedione monoethylene ketal (3.15 g, 20.0 mmol) was dissolved in anhydrous 2-propanol (20 mL), treated with warm malononitrile (Aldrich, 0.70 mL, 11.1 mmol) via syringe, and the reaction was cooled in ice and treated with powdered sodium borohydride (Aldrich, 0.42 g, 11.1 mmol). After stirring for 2 h in ice, the reaction was quenched with water and acidified to pH 6 with 1N aqueous HCl, and the resulting suspension was extracted thrice with dichloromethane. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give a pale yellow oil, which was purified by flash column chromatography on silica gel (gradient elution, 30 to 80% EtOAc in hexanes) giving the title compound as a pale yellow crystalline solid.

Workup

  1. temperaturethe reaction was cooled in ice
  2. customthe reaction was quenched with water
  3. extractionthe resulting suspension was extracted thrice with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a pale yellow oil, which
  9. customwas purified by flash column chromatography on silica gel (gradient elution, 30 to 80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-485e8280090346c19a397bb8fcdd66b8
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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