Triethylamine → (Trimethylsilyl)methyl cyanoacetate

HRID 847266Notes

Reaction equation

HRID 847266 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].[CH3:7][Si:8]([CH2:11]O)([CH3:10])[CH3:9].[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[C:1]([CH2:3][C:4]([O:6][CH2:7][Si:8]([CH3:11])([CH3:10])[CH3:9])=[O:5])#[N:2]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 24477Sodium ThiosulfateHCID 766921-(Trimethylsilyl)methanolHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 14953601(Trimethylsilyl)methyl cyanoacetateYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.5 g (0.1 mole) of cyanoacetic acid, 10.43 g (0.1 mole) of trimethylsilylmethanol, 30.66 g (0.12 mole) of 2-chloro-1-methylpyridinium iodide, 24.3 g (0.24 mole) of triethylamine and 200 ml of tetrahydrofuran were placed in a reaction vessel and reaction was allowed to take place at 50° C. for 3 hours in an argon atmosphere. Thereafter, a 10% aqueous sodium thiosulfate solution was added, followed by extraction with ether. An organic layer obtained was washed with a 10% aqueous sodium thiosulfate solution and then with water, then dried overnight with anhydrous magnesium. Thereafter, the desiccant was filtered off and the solvent was removed under a reduced pressure, followed by vacuum distillation to afford 14.6 g of trimethylsilylmethyl α-cyanoacetate (NCCH2CO2CH2SiMe3) (b.p. 81°-82° C./2 mmHg, yield 85%).

Workup

  1. customreaction
  2. customat 50° C.
  3. customfor 3 hours
  4. extractionfollowed by extraction with ether
  5. customAn organic layer obtained
  6. washwas washed with a 10% aqueous sodium thiosulfate solution
  7. dry with materialwith water, then dried overnight with anhydrous magnesium
  8. filtrationThereafter, the desiccant was filtered off
  9. customthe solvent was removed under a reduced pressure
  10. distillationfollowed by vacuum distillation

Sources & evidence

ORD record
ord-d419141b9bcb4809af3970f7f0a320d0
Source dataset
uspto-grants-1992_08
Patent number
US05140084

Reaction notes

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