Water → HCID 20203551, compound

HRID 1732070Notes

Reaction equation

HRID 1732070 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH3:18])=[CH:14][NH:15]2)=[CH:11][CH:10]=1.[C:19]1(=[O:24])[O:23][CH2:22][CH2:21][CH2:20]1.O>CC(N(C)C)=O.C1(C)C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH3:18])=[CH:14][N:15]2[CH2:22][CH2:21][CH2:20][C:19]([OH:24])=[O:23])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7302Gamma-Butyrolactone3×HCID 11430Potassium CarbonateHCID 3266536-methoxy-3-methyl-1H-indole

Product 1

HCID 20203551HCID 20203551, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 31374DimethylacetamideSolvent

Procedure

Anhydrous potassium carbonate (34.5 g, 0.25 mmol) was added to a solution of 6-methoxy-3-methylindole (16.1 g, 0.1 mol) and γ-butyrolactone (43 g, 0.5 mol) in dimethylacetamide (750 mL). Under mechanical stirring and protected with a drying tube, the reaction mixture was refluxed for 18 hours, more γ-butyrolactone (21.5 g, 0.25 mol) was added, and the reflux was continued for 12 hours. A final portion of γ-butyrolactone (21.5 g, 0.25 mol) was added and the thick suspension was refluxed for another 12 hours, cooled to ~30° C., and poured into water (600 mL). Toluene (600 mL) was added and the 2 layer system was stirred for 15 minutes. The aqueous layer was separated and acidified with concentrated hydrochloric acid. The product was extracted with toluene (3×250 mL). The combined extracts were washed with water (600 mL), dried over MgSO4, filtered, evaporated, and the dark oily residue was chromatographed on silica gel (480 g). Elution with chloroform/hexane (1:1) afforded 18.2 g (74%) of the title compound as a yellowish oil.

Workup

  1. customprotected with a drying tube
  2. temperaturethe reaction mixture was refluxed for 18 hours
  3. temperaturethe thick suspension was refluxed for another 12 hours
  4. temperaturecooled to ~30° C.
  5. stirringthe 2 layer system was stirred for 15 minutes
  6. customThe aqueous layer was separated
  7. extractionThe product was extracted with toluene (3×250 mL)
  8. washThe combined extracts were washed with water (600 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customevaporated
  12. customthe dark oily residue was chromatographed on silica gel (480 g)
  13. washElution with chloroform/hexane (1:1)

Sources & evidence

ORD record
ord-4302586b7f9a46679e0ddc714e3d8f2e
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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