반응 #10771

반응 방정식

hydrochloric acid

4-Hydroxy-2-methoxy-5-thiophen-2-yl-benzaldehyde

4-acetylbenzoic acid

lithium methoxide

→

title compound

수율 5.0%

4-[3E-(4-Hydroxy-2-methoxy-5-thiophen-2-yl-phenyl)-acryloyl]-benzoic acid

수율 5.0%

용매

dimethylformamide methanol

water

ethyl alcohol

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   추출extracted with ethyl acetate (4×25 mL)
3. 3
   건조The combined organic extracts were dried over sodium sulfate
4. 4
   기타evaporated to dryness
5. 5
   기타to yield an orange solid
6. 6
   workup.ADDITIONcontaining residual amounts
7. 7
   기타to remove acid impurity
8. 8
   기타the resulting precipitate was collected
9. 9
   여과on filter paper
10. 10
    기타dried in vacuo

실험 절차

4-Hydroxy-2-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-47B, 0.30 g, 0.86 mmol) and 4-acetylbenzoic acid (0.13 g, 0.86 mmol) were dissolved in a dimethylformamide-methanol solution (6 mL, 7:3). After complete dissolution, lithium methoxide (0.12 g, 3.3 mmol) was added and the resulting red slurry was stirred in the dark at room temperature for 18 h. The mixture was diluted with water (15 mL), acidified with a 1 N hydrochloric acid solution, and extracted with ethyl acetate (4×25 mL). The combined organic extracts were dried over sodium sulfate and evaporated to dryness. The crude oil was subjected to silica gel chromatography (CH2Cl2:MeOH, 20:1) to yield an orange solid containing residual amounts of starting acid. The solid was taken up in ethyl alcohol (5 mL) to remove acid impurity and the resulting precipitate was collected on filter paper and dried in vacuo to yield 0.010 g (5%) of the title compound as an orange solid, mp 243° C. (dec). 1H-NMR (300 MHz, DMSO-d6) δ 8.18–8.23 (m, 3H), 8.06–8.09 (m, 2H), 8.02 (s, 1H), 7.85 (d, 1H, J=15.6 Hz), 7.68 (d, 1H, J=3.6 Hz), 7.47 (d, 1H, J=5.1 Hz), 7.11 (dd, 1H, J=5.1, 3.6 Hz), 6.67 (s, 1H), 4.13 (s, 1H), 3.89 (s, 3H). MS (ESI) m/z=381 ([M+H]30 , 100%). HRMS (ESI) Calcd. for C21H16O5S: 381.0796. Found: 381.0800.

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