Methanol → HCID 68752580, Verbindung

HRID 588984Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588984
C([C:3]1[CH:4]=[C:5]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[N:7][C:8]=1[CH:9]=C)=C.[O:18]=[O+][O-].[BH4-].[Na+].[CH3:23][OH:24]>ClCCl>[OH:24][CH2:23][C:3]1[CH:4]=[C:5]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[N:7][C:8]=1[CH2:9][OH:18]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 24823OzoneHCID 4311764Sodium borohydrideHCID 67026987HCID 67026987, Verbindung

Produkt 1

HCID 68752580HCID 68752580, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 5,6-diethenylpyridine-3-carboxylate (19.0 g, 82 mmol) in dichloromethane (821 mL) at −78° C. was added ozone gas. The ozone bubbled though the solution until saturated (1 h). Nitrogen gas was then bubbled through the solution. The mixture was diluted with methanol (821 mL) and sodium borohydride (7.77 g, 205 mmol) was added. After 15 min, the mixture was quenched with saturated aqueous sodium bicarbonate and washed with dichloromethane (3×). The combined organics were washed with brine, dried with magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→15% methanol dichloromethane) gave the title compound. MS: m/z=240.3 (M+1).

Aufarbeitung

  1. customThe ozone bubbled though the solution until saturated (1 h)
  2. customNitrogen gas was then bubbled through the solution
  3. additionwas added
  4. customthe mixture was quenched with saturated aqueous sodium bicarbonate
  5. washwashed with dichloromethane (3×)
  6. washThe combined organics were washed with brine
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by silica gel chromatography (100% dichloromethane→15% methanol dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-139ab992256f48ef8563f6d6ec674ca2
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227973B2

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