Acrylonitrile → 3-(2-Oxo-1-phenylcyclohexyl)propanenitrile

HRID 714238

反応式

HRID 714238 の反応式
[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](#[N:17])[CH:15]=[CH2:16]>O1CCOCC1>[O:13]=[C:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C:7]1([CH2:16][CH2:15][C:14]#[N:17])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 2

HCID 7855AcrylonitrileHCID 955922-Phenylcyclohexanone

生成物 1

HCID 2633833-(2-Oxo-1-phenylcyclohexyl)propanenitrile収率 77.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

Triton B surfactant (500 μL) was added to a stirred solution of 2-phenylcyclohexanone (5 g, 28.7 mmol) in dioxane (40 mL). A solution of acrylonitrile (1.8 g, 33.9 mmol) in dioxane (5 mL) was added dropwise. A slight exotherm was observed. The solution was stirred at room temperature for 3 h and concentrated. The residue was diluted with EtOAc (50 mL) and washed with water (20 mL, 2×). The EtOAc extract was dried (MgSO4), filtered, and concentrated. The residual oil was chromatographed on a silica gel column. Elution with 2% EtOAc in heptane, followed by 5% EtOAc in heptane afforded 3-(2-oxo-1-phenylcyclohexyl)propanenitrile (Int. 2-A, 5.05 g, 77% yield) as a colorless oil. HPLC: tR=2.73 min, YMC Combi S5 ODS 4.6×50 mm, 4 min gradient, Detection Wave length 220 nm, Starting solvent: 10% aq. MeOH-0.2% H3PO4; Final solvent: 90% aq. MeOH-0.2% H3PO4. LC/MS: m/e 228.26 (M+H)+, 250.14 (M+Na)+.

後処理

  1. concentrationconcentrated
  2. additionThe residue was diluted with EtOAc (50 mL)
  3. washwashed with water (20 mL, 2×)
  4. extractionThe EtOAc extract
  5. dry with materialwas dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residual oil was chromatographed on a silica gel column
  9. washElution with 2% EtOAc in heptane

出典と根拠

ORDレコード
ord-e1b0eb634dda4adaa8a9d40141cdc742
出典データセット
uspto-grants-2015_11
特許番号
US09187437B2

関連ノート

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