Reaktionsgleichung
[CH3:1][C@@H:2]([OH:6])[C@H:3]([OH:5])[CH3:4].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1.C(OCC)(=O)C.[Cl-].[Na+]>[CH2:7]([O:5][C@H:3]([CH3:4])[C@H:2]([OH:6])[CH3:1])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
5.00 g (44.6 mmol) of potassium tert.-butylate was added to a solution of 4.00 g (44.4 mmol) (2R,3R)-butane-2,3-diol in 300 ml THF at room temperature and the mixture was refluxed for 15 minutes. The mixture was cooled to approx. 50° C. and 5.3 ml (44.6 mmol) benzyl bromide was added. It was refluxed for 3 hours, and was then stirred overnight at room temperature. The mixture was diluted with ethyl acetate and sodium chloride solution and then washed with 1N hydrogen chloride solution (1×) and sodium chloride solution (2×). The organic phase was dried (Na2SO4), filtered and concentrated by evaporation. The residue obtained was purified chromatographically (hexane/ethyl acetate 1:1). 3.41 g (18.9 mmol; yield: 43%) of the product was obtained.
Aufarbeitung
- temperaturethe mixture was refluxed for 15 minutes
- temperatureIt was refluxed for 3 hours
- washwashed with 1N hydrogen chloride solution (1×) and sodium chloride solution (2×)
- dry with materialThe organic phase was dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated by evaporation
- customThe residue obtained
- customwas purified chromatographically (hexane/ethyl acetate 1:1)
- custom3.41 g (18.9 mmol; yield: 43%) of the product was obtained
Quellen und Nachweise
- ORD-Eintrag
- ord-86aacf66949b4bfb82e5ce76d2573ccc
- Quelldatensatz
- uspto-grants-2014_05
- Patentnummer
- US08735412B2
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