반응 #1979650

반응 방정식

{[2-(Acetylamino)-1,3-thiazol-4-yl]methyl}(triphenyl)phosphoniumbromide

4-hydroxybenzaldehyde

Water

potassium tert-butoxide

→

N-{4-[2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-2-yl}acetamide

수율 67.5%

용매

N,N-dimethylformamide

ethyl acetate

반응 조건

후처리

1. 1
   온도the mixture was cooled to room temperature
2. 2
   workup.STIRRINGthe mixture was stirred
3. 3
   기타partitioned
4. 4
   추출The aqueous layer was extracted with ethyl acetate
5. 5
   세척the combined organic layer was washed with saturated brine
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The concentrated residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 25 g, ethyl acetate:hexane=4:6→5:5)

실험 절차

{[2-(Acetylamino)-1,3-thiazol-4-yl]methyl}(triphenyl)phosphoniumbromide (261.1 mg, 0.525 mmol) and 4-hydroxybenzaldehyde (183.2 mg, 1.50 mmol) were dissolved in anhydrous N,N-dimethylformamide (2 ml), and potassium tert-butoxide (56.1 mg, 0.50 mmol) was added at 0° C. After stirring at 90° C. for 12 hr, the mixture was cooled to room temperature. Water and ethyl acetate were added, and the mixture was stirred, stood still and then partitioned. The aqueous layer was extracted with ethyl acetate, and the combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 25 g, ethyl acetate:hexane=4:6→5:5) to give N-{4-[2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-2-yl}acetamide (87.9 mg, 0.338 mmol, yield 67.5%) as a white solid.

출처