1,5-Dibromopentane → Ethyl 1-cyanocyclohexane-1-carboxylate

HRID 1922200ノート

反応式

HRID 1922200 の反応式
[C:1]([CH2:3][C:4]([O-:6])=[O:5])#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[C:20](OCC)(=O)[CH3:21]>CN(C=O)C>[CH2:20]([O:5][C:4]([C:3]1([C:1]#[N:2])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:6])[CH3:21]

参加物

6

反応物 4

HCID 81001,5-DibromopentaneHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 1551036Cyanoacetate

生成物 1

HCID 10997650Ethyl 1-cyanocyclohexane-1-carboxylate収率 57%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of cyanoacetate (1 eq) in DMF at 0° C. was slowly added cesium carbonate (2.5 eq), followed by the slow addition of 1,5-dibromopentane. This mixture was allowed to stir for 30 minutes at 0° C. and at room temperature for two hours. The crude reaction mixture was diluted with ethyl acetate and washed three times with water, dried with anhydrous sodium sulfate, filtered, and concentrated. The compound was clean enough to continue without purification. 57% yield. 1H NMR (300 MHz, CDCl3) δ 4.25 (q, 2H), 2.12-1.68 (m, 10H), 1.31 (t, 3H).

後処理

  1. customat 0° C.
  2. customThe crude reaction mixture
  3. washwashed three times with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto continue without purification

出典と根拠

ORDレコード
ord-250348398b5f488c9c00aef0bbb2c6c4
出典データセット
uspto-grants-2012_05
特許番号
US08173689B2

反応ノート

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