Hydrogen Peroxide → HCID 22730343, Verbindung

HRID 1785846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1785846
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[CH2:10])[CH:6]=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=1.B.C(=O)([O-])[O-:23].[Na+].[Na+].OO>C1COCC1.C(OCC)(=O)C>[OH:23][CH2:10][CH2:9][C:7]1[CH:6]=[CH:5][C:4]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:16]=2)=[C:3]([O:2][CH3:1])[CH:8]=1

Komponenten

7

Edukt 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 10340Sodium CarbonateHCID 22730842HCID 22730842, Verbindung

Produkt 1

HCID 22730343HCID 22730343, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of Example 445A (228 mg) and 1M borane in THF (1.2 mL) in THF (2 mL) at room temperature was stirred for 5 hours, and treated sequentially with 2M sodium carbonate (1 mL) and 33% hydrogen peroxide (1 mL). The mixture was heated to 60° C. for 1 hour, diluted with ethyl acetate (100 mL), washed with water (45 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated The concentrate was purified by flash column chromatography on silica gel with 20-40% ethyl acetate/hexanes to provide the desired product.

Aufarbeitung

  1. washwashed with water (45 mL) and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated The concentrate
  5. customwas purified by flash column chromatography on silica gel with 20-40% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-68ccfbd23c22430fbe233f1b14b1e167
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504512B2

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