Dimethyl acetylenedicarboxylate → HCID 13154893, compound

HRID 1621143Notes

Reaction equation

HRID 1621143 reaction equation
[N:1]([CH2:4][Si:5]([CH3:8])([CH3:7])[CH3:6])=[N+:2]=[N-:3].[C:9]([C:15]([O:17][CH3:18])=[O:16])#[C:10][C:11]([O:13][CH3:14])=[O:12]>C1C=CC=CC=1.C(OCC)(=O)C.CCCCCC>[CH3:14][O:13][C:11]([C:10]1[N:3]=[N:2][N:1]([CH2:4][Si:5]([CH3:8])([CH3:7])[CH3:6])[C:9]=1[C:15]([O:17][CH3:18])=[O:16])=[O:12]

Participants

5

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 150751Trimethylsilylmethyl Azide

Product 1

HCID 13154893HCID 13154893, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of azidomethyl-trimethyl-silane (5.0 g, 38.69 mmol) and dimethyl acetylenedicarboxylate (4.74 mL, 38.69 mmol) in benzene (200 mL) was refluxed for 2 h. The solvent was removed in vacuo and the resultant crude material was diluted with water (100 mL), and extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4, filtered, and evaporated in vacuo. The product was obtained after purification by flash chromatography (using silica gel and 20% ethyl acetate/hexane) as colorless liquid (10 g, 36.9 mmol, 95.2%).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe resultant crude material was diluted with water (100 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined organic layer was washed with brine (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe product was obtained

Sources & evidence

ORD record
ord-aac6268c01824c679fec1a09b0d3738f
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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