Acetonitrile → 3-Cyclohexyl-3-oxopropanenitrile

HRID 133479

Reaction equation

HRID 133479 reaction equation
[CH3:1][C:2]#[N:3].[Li]N([Si](C)(C)C)[Si](C)(C)C.[CH:14]1([C:20](OC)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C1COCC1>[CH:14]1([C:20](=[O:21])[CH2:1][C:2]#[N:3])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 20748Methyl cyclohexanecarboxylateHCID 178418261HCID 178418261, compound

Product 1

HCID 113095973-Cyclohexyl-3-oxopropanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.53 mL (10 mmol) of MeCN in 5 ml of THF was cooled in −78° C. bath and 12 mL of 1M LiN(TMS)2 was added. After 5 min, 0.75 mL (5.2 mmol) of methyl cyclohexane carboxylate was added. The cold bath was removed after 1 hr and stirring was continued for another 1 hr. The reaction was acidified with 1.2 N HCl and extracted with ether. The ether layer was washed with brine, dried and concentrated. The residue was chromatographed using a gradient of 10-50% EtOAc-hexane to furnish the desired product.

Workup

  1. customThe cold bath was removed after 1 hr
  2. waitwas continued for another 1 hr
  3. extractionextracted with ether
  4. washThe ether layer was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed

Sources & evidence

ORD record
ord-0fd634d9f9dd4fc187e65e5ee4606e2b
Source dataset
uspto-grants-2008_06
Patent number
US07390835B2

Linked notes

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