Potassium Cyanide → α-Methyl-α-[(trimethylsilyl)oxy]cyclopropaneacetonitrile

HRID 1929804Notes

Reaction equation

HRID 1929804 reaction equation
[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

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 13004Cyclopropyl methyl ketoneHCID 82115Trimethylsilyl cyanide

Product 1

HCID 588006α-Methyl-α-[(trimethylsilyl)oxy]cyclopropaneacetonitrileYield 685.1%

Reagents, catalysts & solvents 1

HCID 2855718-Crown-6Catalyst

Conditions

Temperature
145 °C

Procedure

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 silica gel 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).

Workup

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

Sources & evidence

ORD record
ord-f4408506479849e79d1b7d37327b6915
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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