Sodium Hydroxide → 2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine

HRID 1493043

反応式

HRID 1493043 の反応式
[CH3:1][C:2]1([CH3:24])[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[C:5]2[C:14]([CH3:23])=[C:15]([N+:20]([O-])=O)[C:16]([CH3:19])=[C:17]([CH3:18])[C:4]=2[O:3]1.[OH-].[Na+]>CO.[Zn]>[NH2:20][C:15]1[C:16]([CH3:19])=[C:17]([CH3:18])[C:4]2[O:3][C:2]([CH3:24])([CH3:1])[CH:6]([C:7]3[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=3)[C:5]=2[C:14]=1[CH3:23]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 104962842,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-5-nitro-2,3-dihydrobenzofuran

生成物 1

HCID 106853092,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine収率 61.6%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

実験手順

2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-5-nitro-2,3-dihydrobenzofuran (1.26 g, 3.9 mmol) was dissolved in methanol (30 ml). Zinc powder (1.3 g) and 1N sodium hydroxide (15 ml) were added to the solution and the mixture was heated under reflux for 3 hours. Insoluble materials were filtered off and water was added. The mixture was extracted with ethyl acetate. The extract was washed with water, dried and then the solvent was distilled off. The residue was purified by column chromatography on silica gel (hexane-isopropyl ether, 95:5) and crystallized from hexane to obtain the desired compound (710 mg, yield: 53.7%), m.p. 119°-120° C.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. filtrationInsoluble materials were filtered off
  4. additionwater was added
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. distillationthe solvent was distilled off
  9. customThe residue was purified by column chromatography on silica gel (hexane-isopropyl ether, 95:5)
  10. customcrystallized from hexane

出典と根拠

ORDレコード
ord-5f8eb3dcf419457383fb230c29d9aa24
出典データセット
uspto-grants-1994_12
特許番号
US05376681

関連ノート

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