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

HRID 462511

反応式

HRID 462511 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-26fc452980d64f33bffc69f7d14a2f3a
出典データセット
uspto-grants-1985_05
特許番号
US04515960

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