Reaktion #2074721

Reaktionsgleichung

44

(4S,5S)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-5-[(dimethylphenylsilyl)methyl]-1-cyclopentene-1-methanol

magnesium monoperoxyphthalate

→

crude title compound

Ausbeute 92.3%

(1R,2R,3S,5R)-3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-2-[(dimethylphenylsilyl)methyl]-6-oxabicyclo[3.1.0]hexane-1-methanol

Ausbeute 92.3%

Lösungsmittel

ethyl acetate

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe temperature <0° C
2. 2
   Sonstigethe reaction
3. 3
   Waschenwashed with saturated sodium bisulfite (200 mL), sodium hydroxide (0.5 N, 2×150 mL), brine (150 mL)
4. 4
   Trocknendried over magnesium sulfate
5. 5
   EinengenThe organic layer was concentrated in vacuo to dryness

Vorschrift

To a cooled (0° C.), stirred solution of 44 (14 g, 37.23 mmol) in MeOH (50 mL) was added magnesium monoperoxyphthalate (MPPA, 80% pure, 27.62 g, 44.68 mmol) in six portions over a period of 1 hour, keeping the temperature <0° C. The reaction mixture was stirred at the same temperature for 4 hours to complete the reaction. The reaction mixture was diluted with ethyl acetate (300 mL) and washed with saturated sodium bisulfite (200 mL), sodium hydroxide (0.5 N, 2×150 mL), brine (150 mL) and dried over magnesium sulfate. The organic layer was concentrated in vacuo to dryness to give the crude title compound (13.5 g, 92%)

Quelle