rac-1-O-benzyl-2-O-methyl-3-O-tritylglycerol → 1-O-benzyl-2-O-methylglycerol

HRID 482190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 482190
[CH2:1]([O:8][CH2:9][CH:10]([CH2:13][O:14]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[O:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O>[CH2:1]([O:8][CH2:9][CH:10]([CH2:13][OH:14])[O:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 1

HCID 14584166rac-1-O-benzyl-2-O-methyl-3-O-tritylglycerol

Produkt 1

HCID 1294271-O-benzyl-2-O-methylglycerol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

rac-1-O-Benzyl-2-O-methyl-3-O-tritylglycerol (6.73 g) and 80% HOAc (50 ml) were combined in a 100 ml flask and heated at reflux for three hours. The heat was removed and the reaction mixture was allowed to cool to room temperature. The reaction was neutralized with 10% KOH and extracted with ether. The ether layer was dried (MgSO4) before the solvent was removed in vacuo. Purification of the residue was obtained by column chromatography (150 ml silica gel; hexanes:ethyl acetate, gradient 5:1-0:1). The pure compound 14, rac-1-O-benzyl-2-O-methylglycerol, was obtained as a clear oil (1.84 g, 59.7% yield).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for three hours
  3. customThe heat was removed
  4. extractionextracted with ether
  5. dry with materialThe ether layer was dried (MgSO4) before the solvent
  6. customwas removed in vacuo
  7. customPurification of the residue
  8. customwas obtained by column chromatography (150 ml silica gel; hexanes:ethyl acetate, gradient 5:1-0:1)

Quellen und Nachweise

ORD-Eintrag
ord-fd384ad9e8df46ab84b42abbcee8adee
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05795561

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