Diethyl Oxalate → HCID 12620579, 화합물

HRID 1448891노트

반응식

HRID 1448891 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 12620579HCID 12620579, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-222d72b8bb9140bdbbef3145b70e0ac8
출처 데이터셋
uspto-grants-1980_02
특허 번호
US04188326

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