Reaktion #6055

Reaktionsgleichung

1-benzoyloxy-3-hydroxymethyl-2-methylenecyclobutane

1-Benzoyloxy-3-hydroxymethyl-2-methylenecyclobutane

methylene chloride

methanol

→

title compound

Ausbeute 86.0%

2-Benzoyloxy-4-hydroxymethylcyclobutanone

Ausbeute 86.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeOzone was bubbled through the mixture for 10 minutes, until a persistent blue color
2. 2
   SonstigeExcess ozone was flushed out with nitrogen, 9 mL of dimethyl sulfide
3. 3
   workup.ADDITIONwas added
4. 4
   Temperaturto warm to ambient temperature
5. 5
   workup.STIRRINGstirred for 0.5 h at ambient temperature
6. 6
   Sonstigeevaporated under reduced pressure to a syrup
7. 7
   workup.DISSOLUTIONThe syrup (2.5 g) was dissolved to ~2 mL of methylene chloride
8. 8
   Sonstigepurified on a 1.5×45 cm silica gel column
9. 9
   Wascheneluted @ 5 psi with 100 mL of methylene chloride

Vorschrift

A mixture of 2.09 g (9.5 mmol) of 1-benzoyloxy-3-hydroxymethyl-2-methylenecyclobutane from Step G, 112 mL of methylene chloride and 28 mL of methanol was cooled to -78° C. under a nitrogen atmosphere. Ozone was bubbled through the mixture for 10 minutes, until a persistent blue color was observed. Excess ozone was flushed out with nitrogen, 9 mL of dimethyl sulfide was added and the reaction mixture stirred for 0.5 h at -78° C. The reaction mixture was allowed to warm to ambient temperature, stirred for 0.5 h at ambient temperature and evaporated under reduced pressure to a syrup. The syrup (2.5 g) was dissolved to ~2 mL of methylene chloride and purified on a 1.5×45 cm silica gel column eluted @ 5 psi with 100 mL of methylene chloride, followed by 250 mL of 1% methanol in methylene chloride and 250 mL of 2% methanol in methylene chloride to give 1.79 g (86% yield) of the title compound; MS DCI-NH3M/Z: 221 (M+H)+, 238 (M+NH4)+.

Quelle