4-Methoxyphenylhydrazine hydrochloride → Methyl 3-{5-methoxy-3-[(2-methyl-2-propanyl)sulfanyl]-1H-indol-2-yl}-2,2-dimethylpropanoate

HRID 1590103ノート

反応式

HRID 1590103 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.[C:12]([S:16][CH2:17][C:18](=O)[CH2:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])([CH3:15])([CH3:14])[CH3:13]>CC(O)(C)C>[C:12]([S:16][C:17]1[C:8]2[C:7](=[CH:6][CH:5]=[C:4]([O:3][CH3:2])[CH:9]=2)[NH:10][C:18]=1[CH2:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])([CH3:15])([CH3:14])[CH3:13]

参加物

4

反応物 2

HCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 14980531Methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoate

生成物 1

HCID 14980549Methyl 3-{5-methoxy-3-[(2-methyl-2-propanyl)sulfanyl]-1H-indol-2-yl}-2,2-dimethylpropanoate

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

A solution of 22.7 g 1-(4-methoxyphenyl)hydrazine hydrochloride and 24.6 g methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoate in 500 mL of t-BuOH was heated at reflux under nitrogen for 24 hours. The solvent was removed under reduced pressure and the residue stirred in 900 mL ether. Filtration and evaporation of the Et2O provided an oil which was chromatographed (silica gel; 3% EtOAc in toluene) to provide the title compound as an oil.

後処理

  1. temperatureat reflux under nitrogen for 24 hours
  2. customThe solvent was removed under reduced pressure
  3. filtrationFiltration and evaporation of the Et2O
  4. customprovided an oil which
  5. customwas chromatographed (silica gel; 3% EtOAc in toluene)

出典と根拠

ORDレコード
ord-24fd8d811c804280a8d9bfb8bb582339
出典データセット
uspto-grants-1993_04
特許番号
US05202321

反応ノート

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