Cyanoacetic acid → Acetic acid, cyano-, 2-(trimethylsilyl)ethyl ester

HRID 639151ノート

反応式

HRID 639151 の反応式
[CH3:1][Si:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][OH:5].[C:8]([CH2:10][C:11](O)=[O:12])#[N:9].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>C(OCC)C>[CH3:1][Si:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][O:5][C:11](=[O:12])[CH2:10][C:8]#[N:9]

参加物

6

反応物 4

HCID 9740Cyanoacetic acidHCID 10868DicyclohexylcarbodiimideHCID 180132-(Trimethylsilyl)ethanolHCID 755674-Pyrrolidinopyridine

生成物 1

HCID 11063111Acetic acid, cyano-, 2-(trimethylsilyl)ethyl ester

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

2000 mg (16.91 mmol) 2-(Trimethylsilyl)ethanol are dissolved in 160 ml diethylether. 1307 mg (15.38 mmol) cyanoacetic acid, 3489 mg (16.91 mmol) N,N′-dicyclohexylcarbodiimide and 227 mg (1.54 mmol) 4-(1-pyrrolidinyl)pyridine are added. The mixture is stirred at room temperature for 3 hours under an argon atmosphere and kept at room temperature overnight. The suspension is filtered and the filtrate is washed twice with 5% aqueous acetic acid and twice with water. The organic phase is dried over sodium sulfate, filtered and the solvent is evaporated in vacuo. The residue is re-dissolved in 10 ml hexane and the suspension is filtered over 1 g silica. After evaporation of the solvent, distillation at 0.51 mbar yields the desired product.

後処理

  1. waitkept at room temperature overnight
  2. filtrationThe suspension is filtered
  3. washthe filtrate is washed twice with 5% aqueous acetic acid and twice with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent is evaporated in vacuo
  7. dissolutionThe residue is re-dissolved in 10 ml hexane
  8. filtrationthe suspension is filtered over 1 g silica
  9. customAfter evaporation of the solvent, distillation at 0.51 mbar

出典と根拠

ORDレコード
ord-fb8edf0e53b34f29b6c5117008661137
出典データセット
uspto-grants-2010_04
特許番号
US07691854B2

反応ノート

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