Water → 2-Pentylcyclopentanecarbonitrile

HRID 1674451Notes

Reaction equation

HRID 1674451 reaction equation
S([CH2:11][N+:12]#[C-])(C1C=CC(C)=CC=1)(=O)=O.[CH2:14]([CH:19]1[CH2:23][CH2:22][CH2:21][C:20]1=O)[CH2:15][CH2:16][CH2:17][CH3:18].C(O[K])(C)(C)C.O>COCCOC.C(O)C>[CH2:14]([CH:19]1[CH2:23][CH2:22][CH2:21][CH:20]1[C:11]#[N:12])[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 209592-Pentylcyclopentan-1-oneHCID 161915Tosylmethyl isocyanideHCID 178418922HCID 178418922, compound

Product 1

HCID 673394172-PentylcyclopentanecarbonitrileYield 58.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

27.6 g of tosylmethyl isocyanide and 17 g of 2-pentylcyclopentanone were dissolved in 400 ml of 1,2-dimethoxyethane and 10 ml of ethanol. The solution was cooled to 0° C. with an ice-bath, and 29 g of tBuOK were added in 1 hour maintaining the temperature between 0 and 10° C. After completion of the reaction, the reaction mixture was poured into water and extracted with cyclohexane. The organic layer was washed 3 times with water until neutral pH. Purification by bulb-to-bulb distillation (130° C./0.06 mbar) gave 10.7 g of the pure 2-pentylcyclopentanecarbonitrile.

Workup

  1. temperaturemaintaining the temperature between 0 and 10° C
  2. customAfter completion of the reaction
  3. extractionextracted with cyclohexane
  4. washThe organic layer was washed 3 times with water until neutral pH
  5. customPurification
  6. distillationby bulb-to-bulb distillation (130° C./0.06 mbar)

Sources & evidence

ORD record
ord-c49271624cf74a5784767b8842038fd4
Source dataset
uspto-grants-2011_08
Patent number
US08003084B2

Reaction notes

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