Water → Ethyl 3-{1-(4-bromobenzoyl)-4-hydroxypiperidin-4-yl}alpha,alpha-dimethylphenoxyacetate

반응식

[Br:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[CH2:13][CH2:12][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3O)([OH:14])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-:25].[K+].[K+].O.[CH2:31]([O:33][C:34](=[O:39])[C:35](Br)([CH3:37])[CH3:36])[CH3:32]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:13][CH2:12][C:11]([C:15]3[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=3)[O:25][C:35]([CH3:37])([CH3:36])[C:34]([O:33][CH2:31][CH3:32])=[O:39])([OH:14])[CH2:10][CH2:9]2)=[O:7])=[CH:22][CH:23]=1

참가 물질

반응물 4

HCID 962Water

HCID 11430Potassium Carbonate

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

HCID 152946731-(4-Bromobenzoyl)-4-(2-hydroxyphenyl)-4-hydroxypiperidine

생성물 1

HCID 22399364Ethyl 3-{1-(4-bromobenzoyl)-4-hydroxypiperidin-4-yl}alpha,alpha-dimethylphenoxyacetate수율 86.4%

실험 절차

801 mg of {1-(4-bromobenzoyl)-4-(2-hydroxyphenyl)-4-hydroxypiperidine was stirred for 9 hours at the ambient temperature of 100° C. in the presence of 1.20 g (8.68 mmol) of potassium carbonate in 4.00 g (20.5 ml) of ethylα-bromoisobutyrate. After completion of the reaction, The reaction mixture was cooled, and water was added thereto, followed by extraction with chloroform. Subsequently, the extract was dried over anhydrous sodium sulfate. Chloroform and the remained ethyl α-bromoisobutyrate was distilled off under reduced pressure to obtain 902 mg (86.4%) of ethyl 3-{1-(4-bromobenzoyl)-4-hydroxypiperidin-4-yl}α,α-dimethylphenoxyacetate.