Reaktion #2448897

Reaktionsgleichung

sodium bisulfate

NaHCO3

mCPBA

ketone

tert-Butyl (4-oxoadamantan-1-yl)carbamate

→

lactone

Ausbeute 85.0%

tert-butyl (5-oxo-4-oxatricyclo[4.3.1.13,8]undecan-1-yl]carbamate

Ausbeute 85.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas maintained for 1 h
2. 2
   Extraktionwas extracted with DCM (3×5 mL)
3. 3
   TrocknenThe combined organic layers were dried (Na2SO4)
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue was purified by silica gel chromatography (10/90 to 30/70 EtOAC/hexane)

Vorschrift

Solid NaHCO3 (0.3 mol) and mCPBA (0.3 mmol, 77% purity) were added to a solution of ketone 1C (0.19 mmol) in DCM (5 mL) t 0° C. The reaction mixture was allowed to warm to rt and was maintained for 1 h. The reaction mixture was diluted with a saturated, aqueous solution of sodium bisulfate (10 mL) and was extracted with DCM (3×5 mL). The combined organic layers were dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (10/90 to 30/70 EtOAC/hexane) to provide lactone 13A in 85% yield. Data: LC/MS (ESR) m/z 282 [M+1]+.

Quelle