4-Acetylbenzoic Acid → 4-[3E-{4-Fluoro-3-(thiophen-2-yl)-phenyl}-acryloyl]-benzoic acid

HRID 10630

반응식

HRID 10630 반응식
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[C:10]1[S:11][CH:12]=[CH:13][CH:14]=1.[C:15]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)(=[O:17])[CH3:16].[OH-].[Na+]>CN(C)C=O.O>[F:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:16]/[C:15]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)=[O:17])=[CH:4][C:3]=1[C:10]1[S:11][CH:12]=[CH:13][CH:14]=1

참가 물질

6

반응물 3

HCID 114704-Acetylbenzoic AcidHCID 14798Sodium HydroxideHCID 167688744-Fluoro-3-(thiophen-2-yl)benzaldehyde

생성물 1

HCID 210416224-[3E-{4-Fluoro-3-(thiophen-2-yl)-phenyl}-acryloyl]-benzoic acid수율 53%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

4-Fluoro-3-thiophen-2-yl-benzaldehyde (1.0 g, 4.85 mmol, from Ex-20A) and 4-acetylbenzoic acid (0.80 g, 4.87 mmol) were dissolved in dimethylformamide (55 mL). Sodium hydroxide solution (5 N, 3.88 mL) was added in one portion, and the mixture was stirred at room temperature for 3 h. The reaction was diluted with water (100 mL) and washed with ethyl acetate (100 mL). The aqueous phase was acidified with conc. HCl and extracted with ethyl acetate (2×100 mL). The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. Recrystallization from ethanol provided 0.90 g (53%) of the title compound as a solid, m.p. 242–244° C. 1H-NMR (300 MHz, d6-DMSO) δ 13.31 (bs, 1H), 8.32 (dd, 1H, J=8.2 and 2.0 Hz), 8.24 (d, 2H, J=8.2 Hz), 8.07 (d, 2H, J=7.9 Hz), 7.98 (d, 1H, J=16.1 Hz), 7.92 (m, 1H), 7.80 (d, 1H, J=16.1 Hz), 7.69–7.73 (m, 2H), 7.41 (dd, 1H, 10.8 and 9.2 Hz), 7.20 (m, 1H). MS m/z=352 ([M]+, 50%), 343 (100%). HRMS (EI) Calcd. for C20H13FO3S: 352.0569. Found: 352.0571.

후처리

  1. washwashed with ethyl acetate (100 mL)
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customRecrystallization from ethanol

출처 및 근거

ORD 기록
ord-2a580c9cc4a04d5ca1251353720da926
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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