Reaktion #93567

Reaktionsgleichung

sodium metabisulphite

Peracetic acid

sodium acetate

4-(3-cyclopenten-1-ylmethyl)-1,1'-biphenyl

→

products

3-([1,1'-biphenyl]-4-ylmethyl)-6-oxabicyclo [3.1.0]hexane

Lösungsmittel

acetic acid

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturit was cooled
2. 2
   WaschenThe chloroform layer was washed with water, dilute sodium hydroxide solution, water and brine
3. 3
   Sonstigedried
4. 4
   Sonstigeevaporated

Vorschrift

Peracetic acid in acetic acid (60 ml; 40%) was added over 5 min. to a cooled mixture of sodium acetate (8g) and 4-(3-cyclopenten-1-ylmethyl)-1,1'-biphenyl (20 g) in chloroform (150 ml). The mixture was stirred vigorously at room temperature for 4 h., then it was cooled and a solution of sodium metabisulphite was slowly added. The chloroform layer was washed with water, dilute sodium hydroxide solution, water and brine, dried and evaporated to give a 1:3 mixture (TLC) of two products (20 g). Crystallisation from methylene dichloride-ether gave two crops, rich in the slower running isomer (TLC). Recrystallisation from methylene dichloride/ether gave pure (±)-(1α,3α,5α)-3-([1,1'-biphenyl]-4-ylmethyl)-6-oxabicyclo[3.1.0]hexane (9.6 g), m.p. 130°-132° C.

Quelle