1,2-Dimethoxyethane → HCID 53642966, compound

HRID 129222Notes

Reaction equation

HRID 129222 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:7]=[C:6]2[CH2:22][CH2:23][C:24](O)=[O:25].C(Cl)(C(Cl)=O)=O.[Cl-].[Al+3].[Cl-].[Cl-].C(COC)OC>ClCCCl.O>[OH:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:7]=[C:6]3[CH2:22][CH2:23][C:24](=[O:25])[C:4]=1[C:5]=23

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 19372765HCID 19372765, compound

Product 1

HCID 53642966HCID 53642966, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolvent

Procedure

To a DCE (600 ml) solution of 3-(5-methoxy-1-p-toluenesulfonyl-indol-3-yl)propionic acid (28.9 g, 77 mmol) was added, while stirring under ice-cooling, (COCl)2 (8.3 ml, 95 mmol), and the mixture was stirred for about 2.5 hours at room temperature. The reaction mixture was concentrated, and the residue was dissolved in DCE (100 ml). The solution was added to a suspension of aluminum chloride powder (33.9 g, 254 mmol) in DCE (430 ml) at 5° C. taking 20 minutes. The mixture was left standing as it was at 5° C. for one hour, then stirred for 2.5 hours at room temperature. To the reaction mixture were added, under ice-cooling, dimethoxyethane (300 ml) and water (300 ml). Resulting precipitates were filtered off, then the organic layer was separated. The aqueous layer was subjected to extraction with chloroform (200 ml). The extract solution was combined with the organic layer, which was washed with an aqueous saline solution. The resultant organic layer was dried (anhydrous sodium sulfate), then the solvent was distilled off under reduced pressure to leave 25 g of crude crystals. The crude crystalline product was subjected to silica gel column chromatography, eluting with chloroform, to obtain crystals, followed by recrystallization from chloroform-n-hexane to afford the title compound (m.p.210°-211° C.).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in DCE (100 ml)
  4. waitThe mixture was left
  5. waitwas at 5° C. for one hour
  6. stirringstirred for 2.5 hours at room temperature
  7. additionTo the reaction mixture were added, under ice-
  8. temperaturecooling
  9. customResulting
  10. customprecipitates
  11. filtrationwere filtered off
  12. customthe organic layer was separated
  13. extractionThe aqueous layer was subjected to extraction with chloroform (200 ml)
  14. washwas washed with an aqueous saline solution
  15. dry with materialThe resultant organic layer was dried (anhydrous sodium sulfate)
  16. distillationthe solvent was distilled off under reduced pressure
  17. customto leave 25 g of crude crystals
  18. washeluting with chloroform
  19. customto obtain crystals
  20. customfollowed by recrystallization from chloroform-n-hexane

Sources & evidence

ORD record
ord-58d4129e81644afcb15786268404caf0
Source dataset
uspto-grants-1995_11
Patent number
US05466689

Reaction notes

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