Potassium Cyanide → alpha-Methyl-alpha-((trimethylsilyl)oxy)cyclopropaneacetonitrile

HRID 1159200ノート

反応式

HRID 1159200 の反応式
[CH:1]1([C:4]([CH3:6])=[O:5])[CH2:3][CH2:2]1.[CH3:7][Si:8](C#N)([CH3:10])[CH3:9].[C-:13]#[N:14].[K+]>C1OCCOCCOCCOCCOCCOC1>[CH:1]1([C:4]([O:5][Si:8]([CH3:10])([CH3:9])[CH3:7])([CH3:6])[C:13]#[N:14])[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 9032Potassium CyanideHCID 13004Cyclopropyl methyl ketoneHCID 82115Trimethylsilyl cyanide

生成物 1

HCID 588006alpha-Methyl-alpha-((trimethylsilyl)oxy)cyclopropaneacetonitrile収率 685.1%

試薬・触媒・溶媒 1

HCID 2855718-Crown-6触媒

反応条件

温度
145 °C

実験手順

To a well stirred mixture of cyclopropylmethylketone (27.8 mL, 0.3 mol), trimethylsilylcyanide (55.8 mL, 0.45 mol) and 18-crown-6 (4.87 g, 18.5 mmol) was added potassium cyanide (2.44 g, 37.5 mmol). The temperature rose to ˜100° C. and stirring was continued for 1 h with heating to 145° C. After cooling the mixture was purified by silicagel chromatography (500 g silica, heptane/ethylacetate 6:1) to yield 47.1 g of the title compound as light brown oil, 1H NMR (CDCl3): 0.23 (s, 9H), 0.56 (m, 4H), 1.17 (m, 1H), 1.63 (s, 3H, CH3).

後処理

  1. customrose to ˜100° C.
  2. stirringstirring
  3. temperatureAfter cooling the mixture
  4. customwas purified by silicagel chromatography (500 g silica, heptane/ethylacetate 6:1)

出典と根拠

ORDレコード
ord-4ea9267f5d5b43b7a3f826916acbce6d
出典データセット
uspto-grants-2010_10
特許番号
US07812028B2

反応ノート

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