Methyl levulinate → methyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate

HRID 1683985Notes

Reaction equation

HRID 1683985 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10]N)=[CH:6][CH:5]=1.O=[C:13]([CH3:20])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]>CC(O)=O>[CH3:2][O:3][C:4]1[CH:9]=[C:8]2[C:7](=[CH:6][CH:5]=1)[NH:10][C:13]([CH3:20])=[C:14]2[CH2:15][C:16]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 2

HCID 69354Methyl levulinateHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 82067methyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 4-methoxyphenyl hydrazine hydrochloride (50 g, 0.286M) and methyl 4-oxo-pentanoate (40 mL, 0.315M) in HOAc (500 mL) was stirred for 16 h at reflux. The solvent was removed under vacuum, and the brown residue was partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was washed with H2O and brine, and was then dried (MgSO4) and filtered. Following removal of the solvent, the crude product was purified by flash chromatography (1:20 EtOAc/toluene), to give 48 g of the title compound as a pale brown syrup.

Workup

  1. temperatureat reflux
  2. customThe solvent was removed under vacuum
  3. customthe brown residue was partitioned between EtOAc and saturated NaHCO3 solution
  4. washThe organic layer was washed with H2O and brine
  5. dry with materialwas then dried (MgSO4)
  6. filtrationfiltered
  7. customremoval of the solvent
  8. customthe crude product was purified by flash chromatography (1:20 EtOAc/toluene)

Sources & evidence

ORD record
ord-9502270d9d9e4323969f7d6d0f4163d5
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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