Water → HCID 67338758, compound

HRID 1674450Notes

Reaction equation

HRID 1674450 reaction equation
S([CH2:11][N+:12]#[C-])(C1C=CC(C)=CC=1)(=O)=O.[CH2:14]([CH:21]1[CH2:25][CH2:24][CH2:23][C:22]1=O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(O[K])(C)(C)C.O>COCCOC.C(O)C>[CH2:14]([CH:21]1[CH2:25][CH2:24][CH2:23][CH:22]1[C:11]#[N:12])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 962WaterHCID 87102-HeptylcyclopentanoneHCID 161915Tosylmethyl isocyanideHCID 178418922HCID 178418922, compound

Product 1

HCID 67338758HCID 67338758, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

27.6 g of tosylmethyl isocyanide and 20 g of 2-heptylcyclopentanone 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 (150° C./0.06 mbar) gave 13.4 g of the pure 2-heptylcyclopentanecarbonitrile.

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 (150° C./0.06 mbar)

Sources & evidence

ORD record
ord-6d2e225cc4df46469c8963cb9ce09185
Source dataset
uspto-grants-2011_08
Patent number
US08003084B2

Reaction notes

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