Triethylamine → HCID 11571890, compound

HRID 1669361Notes

Reaction equation

HRID 1669361 reaction equation
O1CC[O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=O.ClC([O:18][CH2:19]C)=O.C([N:23](CC)CC)C>O1CCCC1>[CH3:19][O:18][NH:23][C:9]([C:8]1[CH:7]=[C:6]([CH:14]=[CH:13][CH:12]=1)[CH:2]=[O:3])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 17755226773101-97-6

Product 1

HCID 11571890HCID 11571890, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.63 g of 3-([1,3]dioxolan-2-yl)benzoic acid in 60 ml of tetrahydrofuran were added 3.3 ml of ethyl chloroformate and 4.8 ml of triethylamine under ice-cooling. After stirred for 10 minutes under ice-cooling, insolubles were filtered. This solution was added dropwise to a mixture of 3.63 g of methoxyamine hydrochloride, 20 ml of tetrahydrofuran, 6 ml of triethylamine and 20 ml of dimethylformamide. After stirred at room temperature for 8 hours, insolubles were filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in 30 ml of tetrahydrofuran, and 15 ml of 2 N hydrochloric acid was added dropwise, followed by stirring at room temperature for 8 hours. 20 ml of a 2 N aqueous sodium hydroxide solution was added dropwise under ice-cooling, and this was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 1.50 g of 3-(methoxyaminocarbonyl)benzaldehyde [Compound No. (s)] as a white solid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationinsolubles were filtered
  4. additionThis solution was added dropwise to a mixture of 3.63 g of methoxyamine hydrochloride, 20 ml of tetrahydrofuran, 6 ml of triethylamine and 20 ml of dimethylformamide
  5. stirringAfter stirred at room temperature for 8 hours
  6. filtrationinsolubles were filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. dissolutionThe resulting residue was dissolved in 30 ml of tetrahydrofuran
  9. addition15 ml of 2 N hydrochloric acid was added dropwise
  10. stirringby stirring at room temperature for 8 hours
  11. addition20 ml of a 2 N aqueous sodium hydroxide solution was added dropwise under ice-
  12. temperaturecooling
  13. extractionthis was extracted with ethyl acetate
  14. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  15. dry with materialdried over anhydrous sodium sulfate
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-0e0226cbc8b5429584c0dbe753b3bb9f
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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