Methyl morpholine oxide → 1-(2-Chlorophenyl)-3-(methoxymethoxy)propane-1,2-diol

HRID 1506948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1506948
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/C=C/COCOC.C[N+]1([O-])CC[O:19][CH2:18]C1.[CH3:23][C:24]([CH3:26])=[O:25].C[C:28]([OH:31])(C)C.[OH2:32]>O=[Os](=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=1[CH:23]([OH:32])[CH:24]([OH:25])[CH2:26][O:19][CH2:18][O:31][CH3:28]

Komponenten

5

Edukt 3

HCID 82029Methyl morpholine oxideHCID 86602953Acetone tBuOH WaterHCID 90025785HCID 90025785, Verbindung

Produkt 1

HCID 900190611-(2-Chlorophenyl)-3-(methoxymethoxy)propane-1,2-diolAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 30318Osmium TetroxideKatalysator

Versuchsvorschrift

(E)-1-chloro-2-(3-(methoxymethoxy)prop-1-enyl)benzene (9.1 g, Preparation Example 2) was dissolved in 45 mL of a mixture of acetone/t-BuOH/H2O (5:1:1 V/V). At room temperature, N-methylmorpholine-N-oxide (7.51 g) and OsO4 (0.54 g) were added thereto and stirred for 2-3 hours. When the reaction was completed, the obtained product was washed with water and methylenechloride (MC). Then, the organic layer was dehydrated with anhydrous magnesium sulfate (MgSO4), filtrated, and concentrated under reduced pressure. The crude compound was purified by a silica gel column to produce the title compound (7.42 g, 70˜90%).

Aufarbeitung

  1. washthe obtained product was washed with water and methylenechloride (MC)
  2. filtrationfiltrated
  3. concentrationconcentrated under reduced pressure
  4. customThe crude compound was purified by a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-23dd4a4bbfa7417ab11a7a2c0acff0b8
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221783B2

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