Reacción #56242

Ecuación de reacción

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

Disolventes

water

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with benzene
2. 2
   ExtracciónThe benzene extract
3. 3
   workup.STIRRINGwas shaken with 2 N aqueous sodium hydroxide
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   ExtracciónThe ethyl acetate extract
6. 6
   Lavadowas washed with water
7. 7
   Secadodried over anhydrous sodium sulfate
8. 8
   Otroevaporated to dryness

Procedimiento

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.

Fuente