反応 #56242

反応方程式

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

溶媒

water

tetrahydrofuran

反応条件

後処理

1. 1
   抽出extracted with benzene
2. 2
   抽出The benzene extract
3. 3
   workup.STIRRINGwas shaken with 2 N aqueous sodium hydroxide
4. 4
   抽出extracted with ethyl acetate
5. 5
   抽出The ethyl acetate extract
6. 6
   洗浄was washed with water
7. 7
   乾燥dried over anhydrous sodium sulfate
8. 8
   その他evaporated to dryness

実験手順

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.

出典