Diethyl Oxalate → HCID 12620579, compound

HRID 436862Notes

Reaction equation

HRID 436862 reaction equation
[Na].[CH3:2][C:3]([C:5]1[N:6]([CH3:15])[C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].[C:16](OCC)(=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(O)C>[CH3:15][N:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[C:13]2[O:14][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:2][C:3](=[O:4])[C:5]1=2

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 47121911-(3-hydroxy-1-methyl-1H-indol-2-yl)ethanoneHCID 5360545Sodium

Product 1

HCID 12620579HCID 12620579, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6.0 g (0.26 mole) of sodium metal in 600 ml ab. ethanol was added 18.0 g (0.095 mole) of 3-hydroxy-1-methyl-1H-indol-2-yl methyl ketone, followed by 37.6 g (0.26 mole) of diethyl oxalate, added over 10 min. The mixture was stirred and heated at reflux for 17 hours, cooled and the red di-sodium salt was filtered and washed with cold hexane. The crude salt was added to a solution of 28 ml conc. HCl and 120 ml ab. ethanol, heated at reflux for 30 min., and the mixture was filtered while hot. Cooling the filtrate gave the crude product, which was filtered and then dissolved in 400 ml of chloroform. The chloroform solution was washed 3 times with dilute aqueous NaHCO3, 1 time with water, dried (MgSO4) and evaporated to leave a grey residue. Recrystallization from 15% CHCl3 in hexane gave yellow needles of mpt. 160°-162°.

Workup

  1. additionadded over 10 min
  2. temperatureheated
  3. temperatureat reflux for 17 hours
  4. temperaturecooled
  5. filtrationthe red di-sodium salt was filtered
  6. washwashed with cold hexane
  7. additionThe crude salt was added to a solution of 28 ml conc. HCl and 120 ml ab
  8. temperatureethanol, heated
  9. temperatureat reflux for 30 min.
  10. filtrationthe mixture was filtered while hot
  11. temperatureCooling the filtrate

Sources & evidence

ORD record
ord-2f7fcd30c76f44f396e542219428c326
Source dataset
uspto-grants-1977_06
Patent number
US04028383

Reaction notes

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