반응 #2465230

반응 방정식

1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropanecarboxylic acid methyl ester

Methyl 1-[3-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-5-hydroxy-4-phenyl-4,5-dihydroisoxazol-5-yl]cyclopropanecarboxylate

Compound C

Methyl 1-[3-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-5-hydroxy-4-phenyl-4,5-dihydroisoxazol-5-yl]cyclopropanecarboxylate

sodium bicarbonate

hydrochloric acid

→

1-[3-(4-hydroxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropanecarboxylic acid methyl ester

수율 62.9%

용매

dioxane

반응 조건

후처리

1. 1
   온도The mixture is cooled
2. 2
   추출is extracted with ethyl acetate
3. 3
   건조The organic layer is dried over anhydrous sodium sulfate
4. 4
   여과is filtered
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The concentrate is purified by flash silica gel column chromatography
7. 7
   세척Elution with hexanes-ethyl acetate (9:1 v/v)

실험 절차

To a mixture consisting of 1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropanecarboxylic acid methyl ester (Example 1, Compound C, 7.16 g) in dioxane (120 mL) is added concentrated aqueous hydrochloric acid (30 mL.) The mixture is brought to 100° C. for three hours. The mixture is cooled and is poured into ice water. The mixture is treated with sodium bicarbonate and is extracted with ethyl acetate. The organic layer is dried over anhydrous sodium sulfate and is filtered and concentrated under reduced pressure. The concentrate is purified by flash silica gel column chromatography. Elution with hexanes-ethyl acetate (9:1 v/v) afforded the solid synthetic intermediate 1-[3-(4-hydroxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropanecarboxylic acid methyl ester (3.23 g, 9.63 mmol.)

출처