반응 #56242

반응 방정식

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

용매

water

tetrahydrofuran

반응 조건

후처리

1. 1
   추출extracted with benzene
2. 2
   추출The benzene extract
3. 3
   workup.STIRRINGwas shaken with 2 N aqueous sodium hydroxide
4. 4
   추출extracted with ethyl acetate
5. 5
   추출The ethyl acetate extract
6. 6
   세척was washed with water
7. 7
   건조dried over anhydrous sodium sulfate
8. 8
   기타evaporated to dryness

실험 절차

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.

출처