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

HRID 1683985

反応式

HRID 1683985 の反応式
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]

参加物

4

反応物 2

HCID 69354Methyl levulinateHCID 27239044-Methoxyphenylhydrazine hydrochloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9502270d9d9e4323969f7d6d0f4163d5
出典データセット
uspto-grants-1997_06
特許番号
US05639780

関連ノート

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