Diethylamine → 1-(2,2-Diethoxyethyl)cyclohexane-1-carbonitrile

HRID 462511

Reaction equation

HRID 462511 reaction equation
C(NCC)C.C([Li])CCC.[CH:11]1([C:17]#[N:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[CH2:19]([O:21][CH:22]([O:25][CH2:26][CH3:27])[CH2:23]Br)[CH3:20]>CCCCCC>[CH2:19]([O:21][CH:22]([O:25][CH2:26][CH3:27])[CH2:23][C:11]1([C:17]#[N:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH3:20]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 69834CyanocyclohexaneHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 178418339Butyllithium

Product 1

HCID 132173501-(2,2-Diethoxyethyl)cyclohexane-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

51.7 ml (0.5 mol) of anhydrous diethylamine are added dropwise to 312.5 ml (0.5 mol) of a 15% solution of n-butyl-lithium in hexane at -10° C. under an inert gas blanket. The batch is stirred for 10 minutes and then cooled to -70° C. Within 30 minutes, 54.6 g of cyclohexane-carbonitrile are added dropwise, after a further 30 minutes 98.5 g of bromoacetaldehyde-diethylacetal are added within 1 hour, and the batch is maintained for 24 hours at low temperature. Subsequently, it is warmed to room temperature, given onto 100 g of ice, extracted twice with 500 ml of ethyl acetate, the organic phase is dried over sodium sulfate, concentrated in vacuo, and the residue is subjected to vacuum distillation.

Workup

  1. waitWithin 30 minutes
  2. additionare added within 1 hour
  3. temperaturethe batch is maintained for 24 hours at low temperature
  4. temperatureSubsequently, it is warmed to room temperature
  5. extractionextracted twice with 500 ml of ethyl acetate
  6. dry with materialthe organic phase is dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. distillationthe residue is subjected to vacuum distillation

Sources & evidence

ORD record
ord-26fc452980d64f33bffc69f7d14a2f3a
Source dataset
uspto-grants-1985_05
Patent number
US04515960

Linked notes

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