Ethyl formate → HCID 19882603, compound

HRID 847245Notes

Reaction equation

HRID 847245 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]([CH2:14][NH2:15])[CH2:9][CH2:8][CH2:7]2.[CH:16](OCC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1(C)C=CC=CC=1.O1CCCC1>[ClH:1].[CH3:16][NH:15][CH2:14][CH:10]1[C:11]2[C:6](=[CH:5][C:4]([O:3][CH3:2])=[CH:13][CH:12]=2)[CH2:7][CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 8025Ethyl formateHCID 13197590HCID 13197590, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19882603HCID 19882603, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The product from Example 2 was converted to the free base (15 g) then dissolved in toluene (40 ml). Ethyl formate (70 ml) was added and the reaction refluxed for 2 hr. The solvent was evaporated giving an oil. This was dissolved in dry tetrahydrofuran (THF) (100 ml) and added dropwise to lithium aluminum hydride (3.23 g) in THF, with cooling. Upon complete addition, the reaction was refluxed for 21/2 hr. then stirred an additional 24 hr at room temperature, followed by an additional 3 hrs refluxing. The mixture was cooled in an ice bath, then quenched with H2O (3.3 ml), 15% aq. KOH (3.3 ml) and H2O (9.9 ml) added dropwise. After stirring for 1 hr at room temperature, the reaction was filtered, and evaporated to dryness. The residue was converted to the HCl salt with ethereal/HCl giving 12.9 g desired product.

Workup

  1. temperaturethe reaction refluxed for 2 hr
  2. customThe solvent was evaporated
  3. customgiving an oil
  4. temperaturewith cooling
  5. additionUpon complete addition
  6. temperaturethe reaction was refluxed for 21/2 hr
  7. waitfollowed by an additional 3 hrs
  8. temperaturerefluxing
  9. temperatureThe mixture was cooled in an ice bath
  10. customquenched with H2O (3.3 ml), 15% aq. KOH (3.3 ml) and H2O (9.9 ml)
  11. additionadded dropwise
  12. stirringAfter stirring for 1 hr at room temperature
  13. filtrationthe reaction was filtered
  14. customevaporated to dryness

Sources & evidence

ORD record
ord-bd409c096bd84192900e3b33bec6c770
Source dataset
uspto-grants-1992_08
Patent number
US05140040

Reaction notes

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