Reaktion #1279118

Reaktionsgleichung

sodium hypochlorite

6-bromo-1H-indene

4-(3-phenylpropyl)pyridine N-oxide

sodium hypochlorite

→

4-Bromo-6,6a-dihydro-1aH-indeno[1,2-b]oxirene

Lösungsmittel

water

brine

methylene chloride

methylene chloride

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITThe reaction was kept at 0° C. for 1 h
2. 2
   Temperaturto warm up to room temperature
3. 3
   workup.STIRRINGstirred at room temperature overnight
4. 4
   Extraktionextracted with methylen chloride (4×40 mL)
5. 5
   TrocknenThe combined extracts were dried over anhydrous Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated under reduced pressure
8. 8
   SonstigeThe crude product was used directly for the next reaction

Vorschrift

To a solution of 4-(3-phenylpropyl)pyridine N-oxide (68.88 mg, 0.323 mmol) in methylene chloride (6.00 mL) was added (S,S)-(+)-N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino-manganese(III) chloride (58.62 mg, 0.09.23 mmol) and 2.0 M of sodium hypochlorite in water (4.00 mL) at 0° C. The resulting brown suspension was stirred at 0° C. for 15 min. To the cooled suspension was added a solution of 6-bromo-1H-indene (900 mg, 4.6141 mmol) in methylene chloride (6.00 mL) at 0° C. with simultaneous addition of 2.0 M of sodium hypochlorite in water (4.00 mL) at 0° C. The reaction was kept at 0° C. for 1 h. The reaction was allowed to warm up to room temperature and then stirred at room temperature overnight. The reaction mixture was poured into brine and then extracted with methylen chloride (4×40 mL). The combined extracts were dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude product was used directly for the next reaction. The ratio of the two diastereomers was 8/1.

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