Sodium hydride → 9-[(3-Methylphenyl)methyl]-2-methyl-4-hydroxy-5-carbomethoxy carbazole

HRID 567237

반응식

HRID 567237 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:21]3[CH2:20][CH:19]([CH3:22])[CH2:18][C:17](=[O:23])[C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][C:14]=3[C:24]([O:26][CH3:27])=[O:25])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].C1(S(OC)=O)C=CC=CC=1>O1CCOCC1.C(O)(=O)C.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:21]3[CH:20]=[C:19]([CH3:22])[CH:18]=[C:17]([OH:23])[C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][C:14]=3[C:24]([O:26][CH3:27])=[O:25])[CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 2759784Methyl benzenesulfinateHCID 227383569-[(3-methylphenyl)methyl]-5-carbomethoxy-2-methyl-1,2-dihydrocarbazol-4(3H)-one

생성물 1

HCID 227381449-[(3-Methylphenyl)methyl]-2-methyl-4-hydroxy-5-carbomethoxy carbazole수율 66%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매2회

실험 절차

To a solution of 9-[(3-methylphenyl)methyl]-5-carbomethoxy-2-methyl-1,2-dihydrocarbazol-4(3H)-one (1.41 g, 3.89 mM) in 13 ml dioxane was added 60% sodium hydride in mineral oil (0.36 g, 8.95 mM). The reaction was stirred 6 minutes, then methyl benzenesulfinate (0.81 ml, 6.22 mM) was added. The reaction was stirred an additional 6 hours, then diluted with 20 ml dioxane and 0.51 ml acetic acid. The mixture was refluxed 30 minutes, diluted with ethyl acetate, and extracted with saturated NaHCO3, brine, then water. After drying (NaSO4), evaporation in vacuo afforded 2.30 g. The mixture was purified by column chromatography on silica gel (elution with toluene/methylene chloride) to afford 0.92 g (66%) of 9-[(3-methylphenyl)methyl]-2-methyl-4-hydroxy-5-carbomethoxy carbazole. 1H NMR (CDCl3) δ 10.45 (s, 1H), 8.0 (d, J=8 Hz, 1H), 7.55 (d, J=8 Hz, 1H), 7.4 (dd, J=8 and 8 Hz, 1H), 7.4 (dd, J=8 and 8 Hz, 1H), 7.05 (d, J=8 HZ, 1H), 6.9 (s, 1H), 6.85 (d, J=8 Hz, 1H), 6.75 (s, 1H), 6.7 (s, 1H), 5.45 (s, 2H), 4.1 (s, 3H), 2.4 (s, 3H), 2.25 (s, 3H). MS (ES) m/e 328, 360.

후처리

  1. stirringThe reaction was stirred an additional 6 hours
  2. temperatureThe mixture was refluxed 30 minutes
  3. extractionextracted with saturated NaHCO3, brine
  4. customAfter drying
  5. custom(NaSO4), evaporation in vacuo
  6. customafforded 2.30 g
  7. customThe mixture was purified by column chromatography on silica gel (elution with toluene/methylene chloride)

출처 및 근거

ORD 기록
ord-abecfa8ce51f430a845d187baf20d432
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06177440B1

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