Reaktion #56242

Reaktionsgleichung

hydrochloric acid

sodium hydride

9-formyl-9,10-dihydro-9,10-methanoanthracene

β-carboxyethyltriphenylphosphonium chloride

dimethylsulfoxide

→

γ-(9,10-dihydro-9,10-methano-9-anthryl)-β-butenoic acid

Lösungsmittel

water

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with benzene
2. 2
   ExtraktionThe benzene extract
3. 3
   workup.STIRRINGwas shaken with 2 N aqueous sodium hydroxide
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   ExtraktionThe ethyl acetate extract
6. 6
   Waschenwas washed with water
7. 7
   Trocknendried over anhydrous sodium sulfate
8. 8
   Sonstigeevaporated to dryness

Vorschrift

To a mixture of 9-formyl-9,10-dihydro-9,10-methanoanthracene (110 mg) and β-carboxyethyltriphenylphosphonium chloride (186 mg) in dimethylsulfoxide (2 ml) and tetrahydrofuran (2 ml) was added 65.4% sodium hydride dispersion in mineral oil (37 mg) at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. for 6 hours, diluted with water, acidified with hydrochloric acid and extracted with benzene. The benzene extract was shaken with 2 N aqueous sodium hydroxide. The basic layer was acidified with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness to give γ-(9,10-dihydro-9,10-methano-9-anthryl)-β-butenoic acid. M.P. 166°-167° C.

Quelle