Sodium hydride → 9-[(Phenyl)methyl]-4-hydroxy-5-carbomethoxy carbazole

HRID 567262

반응식

HRID 567262 반응식
[C:1]1([CH2:7][N:8]2[C:20]3[CH2:19][CH2:18][CH2:17][C:16](=[O:21])[C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][C:13]=3[C:22]([O:24][CH3:25])=[O:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1(S(OC)=O)C=CC=CC=1>O1CCOCC1.C(O)(=O)C.C(OCC)(=O)C>[C:1]1([CH2:7][N:8]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([OH:21])[C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][C:13]=3[C:22]([O:24][CH3:25])=[O:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 2759784Methyl benzenesulfinateHCID 223377289-[(phenyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one

생성물 1

HCID 223377169-[(Phenyl)methyl]-4-hydroxy-5-carbomethoxy carbazole수율 81%

시약·촉매·용매 3

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

실험 절차

To a solution of the 9-[(phenyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one (2.87 g, 8.61 mM) in 29 ml dioxane was added 60% sodium hydride in mineral oil (0.79 g, 19.8 mM). The reaction was stirred 8 minutes, then methyl benzenesulfinate (1.80 ml, 13.8 mM) was added. The reaction was stirred an additional 1.5 h, then diluted with 43 ml dioxane and 1.13 ml acetic acid. The mixture was refluxed 1 h, diluted with ethyl acetate, and extracted with sat'd NaHCO3 two times, then with brine. After drying (NaSO4), evaporation in vacuo afforded 4.90 g. The mixture was purified by column chromatography on silica gel (elution with toluene/methylene chloride) to afford 2.31 g (81%) of the 9-[(phenyl)methyl]-4-hydroxy-5-carbomethoxy carbazole. 1H NMR (DMSO-d6) δ 10.25 (s, 1H), 7.7 (d, 1H, J=8 Hz), 7.4 (t, 1H, J=8 Hz), 7.4-7.0 (m, 8H), 6.6 (d, 1H, J=8 Hz), 5.6 (s, 2H), and 3.8 (s, 3H). IR (CHCl3, cm−1) 1723, 1685, 1621, 1597, 1568, 1496, 1453, 1442, 1392, 1286, 1267, 1156, and 1138. MS (ES) m/e 330, 332.

후처리

  1. stirringThe reaction was stirred an additional 1.5 h
  2. temperatureThe mixture was refluxed 1 h
  3. extractionextracted with sat'd NaHCO3 two times
  4. customAfter drying
  5. custom(NaSO4), evaporation in vacuo
  6. customafforded 4.90 g
  7. customThe mixture was purified by column chromatography on silica gel (elution with toluene/methylene chloride)

출처 및 근거

ORD 기록
ord-c9308454aa0f41988482530667411ddf
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06177440B1

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