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

HRID 585586

Reaktionsgleichung

Reaktionsgleichung von HRID 585586
[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

Komponenten

7

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

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 hours, then diluted with 43 ml dioxane and 1.13 ml acetic acid. The mixture was refluxed 1 hour, diluted with ethyl acetate, and extracted with saturated 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.

Aufarbeitung

  1. stirringThe reaction was stirred an additional 1.5 hours
  2. temperatureThe mixture was refluxed 1 hour
  3. extractionextracted with saturated 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)

Quellen und Nachweise

ORD-Eintrag
ord-d1969be3f8aa4c0b99349b13dbfbea8a
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06933313B2

Verknüpfte Notizen

Wird geladen…