Reaktion #2015859

Reaktionsgleichung

(4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(iodomethyl)-tetrahydropyran-2-one

EtOAc

water

→

((2S,4R)-4-(tert-butyldimethylsilyloxy)-6-oxo-tetrahydro-2H-pyran-2-yl)methyl acetate

Ausbeute 92.6%

Lösungsmittel

AcOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture is filtered through diatomite
2. 2
   Filtrationfilter medium (Celite®)
3. 3
   SonstigeThe obtained filtrate is evaporated
4. 4
   Sonstigeto afford the residue
5. 5
   SonstigeThe organic layer is separated
6. 6
   Waschenthe aqueous layer is washed again with EtOAc (5×150 mL)
7. 7
   WaschenThe combined organic layers are washed with water (4×300 mL), brine (5×300 mL)
8. 8
   Trocknendried over anhydrous MgSO4
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated under the reduced pressure

Vorschrift

To a solution of (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(iodomethyl)-tetrahydropyran-2-one (40.00 g, 108.0 mmol) in AcOH (660 mL), AgOAc (20.03 g, 118.8 mmol) is added. The resultant mixture is then heated at 125° C. for 6 hours. The reaction mixture is filtered through diatomite filter medium (Celite®). The obtained filtrate is evaporated to afford the residue. To this residue, EtOAc (500 mL) and water (600 mL) are added. The organic layer is separated and the aqueous layer is washed again with EtOAc (5×150 mL). The combined organic layers are washed with water (4×300 mL), brine (5×300 mL) and dried over anhydrous MgSO4, filtered and concentrated under the reduced pressure to afford 30.28 g (92.6%) of ((2S,4R)-4-(tert-butyldimethylsilyloxy)-6-oxo-tetrahydro-2H-pyran-2-yl)methyl acetate as yellow oil (HPLC purity 98%).

Quelle