Diethyl Oxalate → HCID 12620579, compound

HRID 371656Notes

Reaction equation

HRID 371656 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 6.0g (0.26 mole) of sodium metal in 600ml ab. ethanol was added to 18.0g (0.095 mole) of 3-hydroxy-1-methyl-1H-indol-2-yl methyl ketone, followed by 37.6g (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 28ml conc. HCl and 120ml 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 400ml 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 28ml conc. HCl and 120ml 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-707b3b86900046de81c6fdbc07b0d956
Source dataset
uspto-grants-1978_05
Patent number
US04087443

Reaction notes

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