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

HRID 620922

反応式

HRID 620922 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, under protective gas at -10° C., to 312.5 ml (0.5 mol) of a 15% strength solution of n-butyllithium in hexane. The mixture is stirred for 20 minutes and then cooled to -70° C. 54.6 g of cyclohexanecarbonitrile are added dropwise over the course of 30 minutes and, after a further 30 minutes, 98.5 g of bromoacetaldehyde diethyl acetal are added within 1 hour and the mixture is left at low temperature for 24 hours. It is then warmed to room temperature, 100 g of ice are added, and the mixture is extracted twice with 500 ml of ethyl acetate, and the organic phase is dried over sodium sulfate, evaporated in vacuo and the residue is subjected to vacuum distillation.

後処理

  1. waitthe mixture is left at low temperature for 24 hours
  2. temperatureIt is then warmed to room temperature
  3. extractionthe mixture is extracted twice with 500 ml of ethyl acetate
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. customevaporated in vacuo
  6. distillationthe residue is subjected to vacuum distillation

出典と根拠

ORDレコード
ord-c95d3c5d99e543bf941100058e7e16a4
出典データセット
uspto-grants-1989_04
特許番号
US04822894

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