반응 #10774

반응 방정식

hydrochloric acid

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

4-acetylbenzoic acid

lithium methoxide

→

title compound

수율 15.3%

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

수율 15.3%

용매

dimethylformamide methanol

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   추출extracted with ethyl acetate (3×20 mL)
3. 3
   건조The combined organic extracts were dried over sodium sulfate
4. 4
   기타evaporated to dryness
5. 5
   온도warmed to 60° C.
6. 6
   기타to obtain complete
7. 7
   workup.DISSOLUTIONdissolution
8. 8
   온도to cool to room temperature
9. 9
   온도with heating
10. 10
    기타The resulting precipitate was collected
11. 11
    여과on filter paper
12. 12
    기타dried in vacuo

실험 절차

2-Hydroxy-4-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-29B, 0.10 g, 0.43 mmol) and 4-acetylbenzoic acid (0.070 g, 0.43 mmol) were dissolved in a dimethylformamide-methanol solution (2.8 mL, 7:3). After complete dissolution, lithium methoxide (0.065 g, 1.7 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 (10 mL), acidified with a 1 N hydrochloric acid solution, and extracted with ethyl acetate (3×20 mL). The combined organic extracts were dried over sodium sulfate and evaporated to dryness. The crude oil was taken up in ethyl alcohol (5 mL) and warmed to 60° C. to obtain complete dissolution and allowed to cool to room temperature. Note: the compound appears to decompose with heating. The resulting precipitate was collected on filter paper and dried in vacuo to yield 0.025 g (15%) of the title compound as a dark yellow solid, mp 125° C. (dec). 1H-NMR (300 MHz, DMSO-d6) δ 10.73 (s, 1H), 8.18–8.22 (m, 3H), 8.09 (d, 2H, J=8.1 Hz), 8.05 (s, 1H), 7.87 (d, 1H, J=14.7 Hz), 7.60 (d, 1H, J=3.0 Hz), 7.49 (d, 1H, J=4.2 Hz), 7.11 (dd, 1H, J=4.2, 3.0 Hz), 6.67 (s, 1H), 3.90 (s, 3H). MS (ESI) m/z=381 ([M+H]+, 100%). Anal. Calcd. for C21H16O5S.EtOH: C, 64.77; H, 5.20; S, 7.52. Found: C, 64.68; H, 5.00; S, 7.77.

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