Ethyl Acetate → HCID 21846284, compound

HRID 343848Notes

Reaction equation

HRID 343848 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)(=[O:3])[CH3:2].[H-].[Na+].[C:15](OCC)(=[O:17])[CH3:16]>>[NH:8]1[C:9]2[C:5](=[C:4]([C:1](=[O:3])[CH2:2][C:15](=[O:17])[CH3:16])[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7]1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 130046731-(1H-Indol-4-yl)ethan-1-one

Product 1

HCID 21846284HCID 21846284, compound

Procedure

4-Acetylindole (0.101 g) was refluxed in 5 mL of ethyl acetate. Sodium hydride (0.20 g, 60% oil dispersion) was added in portions to the refluxing solution until thin layer chromatography analysis showed complete consumption of the starting material. The reaction mixture was quenched with water and acidified to pH 3. The ethyl acetate layer was dried (magnesium sulfate) and concentrated to give a crude product. The crude material was chromatographed on silica gel, eluting with hexane/ethyl acetate to give 1-(1H-indol-4-yl)-1,3-butanedione (0.104 g), a compound of formula (11), m.p. 104°-105° C.

Workup

  1. customconsumption of the starting material
  2. customThe reaction mixture was quenched with water
  3. dry with materialThe ethyl acetate layer was dried (magnesium sulfate)
  4. concentrationconcentrated
  5. customto give a crude product
  6. customThe crude material was chromatographed on silica gel
  7. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-8801d30994174d00877f81bdb97836c4
Source dataset
uspto-grants-1999_01
Patent number
US05863924

Reaction notes

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