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

HRID 639151
Notes
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Reaction equation

HRID 639151 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fb8edf0e53b34f29b6c5117008661137
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07691854B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes