Water → tert-Butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2173930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173930
[CH3:1][O:2][C:3]1[C:4]([CH:20]=CC)=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:7]=[CH:6]2.O.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=[O:33].[Na+]>O1CCOCC1.[Os](=O)(=O)(=O)=O>[CH:20]([C:4]1[C:3]([O:2][CH3:1])=[CH:11][C:10]([CH3:12])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[O:33]

Komponenten

7

Edukt 4

HCID 962WaterHCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 86701481tert-Butyl 5-methoxy-7-methyl-4-(prop-1-en-1-yl)-1H-indole-1-carboxylate

Produkt 1

HCID 72191522tert-Butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

tert-Butyl 5-methoxy-7-methyl-4-(prop-1-en-1-yl)-1H-indole-1-carboxylate (0.29 g, 0.97 mmol) was dissolved in dioxane (7.27 mL) and water (2.4 mL) and 2,6-lutidine (0.23 mL, 1.94 mmol) was added followed by osmium tetroxide (0.24 mL, 0.019 mmol) and sodium periodate (0.83 g, 3.88 mmol) at 0° C. The reaction was removed from the ice bath and let stir at room temperature for 1 hour. The reaction was diluted with methylene chloride and water. The organic layer was separated, dried over sodium sulfate and then concentrated. The resulting residue was absorbed onto silica and then purified by silica gel flash chromatography (0-50% ethyl acetate/heptanes) to provide the title compound. MS (ESI+) m/z 290.1 (M+H).

Aufarbeitung

  1. customThe reaction was removed from the ice bath
  2. additionThe reaction was diluted with methylene chloride and water
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was absorbed onto silica
  7. custompurified by silica gel flash chromatography (0-50% ethyl acetate/heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-8862e0e36afc4bcdb63eeb26c7eb0a64
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056874B2

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