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

HRID 1493043

반응식

HRID 1493043 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5f8eb3dcf419457383fb230c29d9aa24
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05376681

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