Diethyl Ether → HCID 14091463, compound

HRID 904698Notes

Reaction equation

HRID 904698 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]=1[OH:14])[N:10]=[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:8]=[C:7]2[N:23]([CH3:25])[CH3:24])(=[O:3])[CH3:2].[C:26](OCC)(=O)[C:27]([O:29][CH2:30][CH3:31])=[O:28].CCOCC.[H-].[Na+]>CN(C)C=O.Cl.O>[CH3:25][N:23]([CH3:24])[C:7]1[C:6]2[C:11](=[C:12]([CH2:15][CH2:16][CH3:17])[C:13]3[O:14][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:2][C:1](=[O:3])[C:4]=3[CH:5]=2)[N:10]=[C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:8]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 135773199HCID 135773199, compound

Product 1

HCID 14091463HCID 14091463, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A mixture of the product of step (b) (1.6 g; 4.8426 mmole) and diethyl oxalate (5.7 g; 39.041 mmole; 5.3 ml) in dry dimethylformamide (60 ml) was added slowly to a stirring suspension of ether washed sodium hydride (0.29 g; 12.0808 mmole) in dry dimethylformamide (10 ml) under nitrogen. After the addition, the mixture was allowed to stir for 7 hours. The reaction mixture was poured onto ice and was then acidified with dilute hydrochloric acid. The pH of the mixture was adjusted to about 6 before being extracted into chloroform. This was washed with water, dried and evaporated to give a yellow solid. The solid was taken up in ethanolic hydrogen chloride (50 ml) and heated to reflux on the steambath for 3 hours. The solution was cooled, treated with water and then concentrated. The pH of the mixture was adjusted to about 7 and then extracted into chloroform. The extract was washed with water, dried and evaporated, to give a brown solid.

Workup

  1. additionAfter the addition
  2. additionThe reaction mixture was poured onto ice
  3. extractionbefore being extracted into chloroform
  4. washThis was washed with water
  5. customdried
  6. customevaporated
  7. customto give a yellow solid
  8. temperatureheated
  9. temperatureto reflux on the steambath for 3 hours
  10. temperatureThe solution was cooled
  11. concentrationconcentrated
  12. extractionextracted into chloroform
  13. washThe extract was washed with water
  14. customdried
  15. customevaporated
  16. customto give a brown solid

Sources & evidence

ORD record
ord-3a49a426ef224d1caf3b8db1f1afd594
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

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