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

HRID 327241ノート

反応式

HRID 327241 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収率 39.3%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

A mixture containing 4-methoxyphenyl hydrazine HCl (70.66 g, 0.405 mol) and methyl 5-(t-butylthio)-2,2-dimethyl-4-oxopentanoate (99.54 g 0.405 mol) in tBuOH (400 ml) was heated at a gentle reflux for 48 hours. The mixture was allowed to cool to RT and the precipitated NH4Cl was removed by filtration. The residue was concentrated and fractionated on a plug of silica using EtOAc/hexane (1:3) as eluent. Evaporation of the appropriate fraction gave an orange-brown solid which was crystallized from EtOH (100 ml). Yield from two crops afforded 55.6 g of the title compound.

後処理

  1. temperaturewas heated at
  2. temperaturea gentle reflux for 48 hours
  3. customthe precipitated NH4Cl was removed by filtration
  4. concentrationThe residue was concentrated
  5. customEvaporation of the appropriate fraction
  6. customgave an orange-brown solid which
  7. customwas crystallized from EtOH (100 ml)
  8. customYield from two crops

出典と根拠

ORDレコード
ord-f74fa5c5df50428d94c620f53e53ba69
出典データセット
uspto-grants-1993_12
特許番号
US05272145

反応ノート

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