CH3CCH→cH2cH2cH2CH3 I2CH,Ch,Ch CH3CCH, CooCH,CH CH2CHBr CH2CH3 Acetoacetic ester 乙酰乙酸乙 Na )NaoCHCH3 CH3 CH,CH CH2Br CH3CCHCOOCHCH CH, CCHCOOCHCH S、2 Acetoacetic ester 乙酰乙酸乙酯 Nucleophile reagent CHaCCH-CH, CH, CH, CH3 I)NaOCH2CH3 CH3CH CH3CC—cH2CH2CH2cH3 COOCH2 CH3 COOCH2 CH3 o CH2CH3 CH2CH 1)NaoH CH3CC—cH2cH2cH2cH CH3CC--CH2CH2CH2CH2H301 水解 CooCH CH CooNa OCH2CH3 CH2 CH heat CH3CC—cH2cH2CH2cH3 H CH3 CCH-CH2CH2CH2CH3 CO, COQHCH3 CCH O CH2 CH2 CH2 CH3 CH2 CH3 CH3CCH2COOCH2CH3 O 1) NaOCH2CH3 CH3CCHCOOCH2CH3 O - Na + Acetoacetic ester 乙 酰 乙 酸 乙 酯 Nucleophile reagent CH3CH2CH2CH2 Br CH3CCH SN2 O COOCH2CH3 CH2CH2CH2CH3 CH3CH2 1) NaOCH2CH3 CH3CC O COOCH2CH3 CH2CH2CH2CH3 - Na + Br SN2 CH3CCH2COOCH2CH3 O Acetoacetic ester 乙 酰 乙 酸 乙 酯 + CH3CH2CH2CH2 Br CH3CH2Br 1) NaOH 2) H3O+ CH3CC O COONa CH2CH2CH2CH3 CH3CC O COOH CH2CH2CH2CH3 heat - CO2 CH3CCH O CH2CH2CH2CH3 脱 羧 水 解 CH3CC O COOCH2CH3 CH2CH2CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH2CH3