반응 #1979692

반응 방정식

Hydrochloric acid

4-(1,3-dioxolan-2-yl)-5-(trimethylsilyl)thiophene-2-carbaldehyde

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

potassium tert-butoxide

→

N-(4-{2-[4-(1,3-dioxolan-2-yl)-5-(trimethylsilyl)thiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamide

수율 95.0%

용매

water

N,N-dimethylformamide

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred for 1 hr
2. 2
   추출the mixture was extracted 3 times with ethyl acetate
3. 3
   세척The combined organic layer was washed with saturated brine
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 200 g, ethyl acetate:dichloromethane=1:6)

실험 절차

To a solution of {[2-(acetylamino)-1,3-thiazol-4-yl]methyl}(triphenyl)phosphoniumbromide (7.970 g, 16.03 mmol) in anhydrous N,N-dimethylformamide (32 ml) was added potassium tert-butoxide (3.687 g, 32.86 mmol) at 0° C., and the mixture was stirred for 1 hr. A solution of 4-(1,3-dioxolan-2-yl)-5-(trimethylsilyl)thiophene-2-carbaldehyde (2.740 g, 10.69 mmol) in anhydrous N,N-dimethylformamide (6 ml) was added dropwise, and the mixture was stirred for 1 hr. 1M Hydrochloric acid (17.0 ml) and iced water (170 ml) were added, and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 200 g, ethyl acetate:dichloromethane=1:6) to give N-(4-{2-[4-(1,3-dioxolan-2-yl)-5-(trimethylsilyl)thiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamide (4.010 g, 10.16 mmol, yield 95.0%) as an off-white solid.

출처