Reaktion #5807

Reaktionsgleichung

water

diethyl ether

(R)-1,1-dimethylethyl 6-cyano-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-oxohexanoate

tetrabutylammonium fluoride

→

(R)-1,1-dimethylethyl 6-cyano-5-hydroxy-3-oxohexanoate

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added
2. 2
   Sonstigethe layers separated
3. 3
   TrocknenThe organic layer is dried (magnesium sulfate)
4. 4
   Filtrationfiltered through a plug of silica gel with the aid of anhydrous diethyl ether
5. 5
   SonstigeThe solvent is removed under a vacuum

Vorschrift

A solution of crude (R)-1,1-dimethylethyl 6-cyano-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-oxohexanoate, 43 g (0.126 mol) in 350 mL of tetrahydrofuran is treated with 213 mL of tetrabutylammonium fluoride solution (1.0M in hexane). The resulting mixture is stirred for five hours, at 25° C. The mixture is treated with 500 mL of water, 300 mL of diethyl ether is added, and the layers separated. The organic layer is dried (magnesium sulfate) and then filtered through a plug of silica gel with the aid of anhydrous diethyl ether. The solvent is removed under a vacuum to obtain 21 g of crude (R)-1,1-dimethylethyl 6-cyano-5-hydroxy-3-oxohexanoate with acceptable NMR, MS and IR spectra.

Quelle