4-Acetylbenzoic Acid → 4-[3E-(4-Pyrrolidin-1-yl-3-thiophen-2-yl-phenyl)-acryloyl]-benzoic acid

HRID 10629

反応式

HRID 10629 の反応式
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][C:7]=2[C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1)(=[O:21])[CH3:20].[OH-].[Na+]>CN(C)C=O.O>[N:1]1([C:6]2[CH:13]=[CH:12][C:9](/[CH:10]=[CH:20]/[C:19]([C:22]3[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=3)=[O:21])=[CH:8][C:7]=2[C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 114704-Acetylbenzoic AcidHCID 14798Sodium HydroxideHCID 219810554-Pyrrolidin-1-yl-3-(thiophen-2-yl)-benzaldehyde

生成物 1

HCID 210416254-[3E-(4-Pyrrolidin-1-yl-3-thiophen-2-yl-phenyl)-acryloyl]-benzoic acid収率 13%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

4-Pyrrolidin-1-yl-3-(thiophen-2-yl)-benzaldehyde (400 mg, 1.55 mmol) from Ex-20B and 4-acetylbenzoic acid (255 mg, 1.55 mmol) were dissolved in dimethylformamide (30 mL). Sodium hydroxide solution (5 N, 1.25 mL) was added in one portion, and the mixture was stirred at room temperature overnight. 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. Silica gel chromatography (100% ethyl acetate) followed by recrystallization from ethanol provided 80 mg (13%) of the title compound as a solid, m.p. 212–214° C. with decomposition. 1H-NMR (300 MHz, CDCl3) δ 8.21 (d, 2H, J=8.4 Hz), 7.06 (d, 2H, J=8.4 Hz), 7.80 (d, 1H, J=15.3 Hz), 7.58 (d, 1H, J=1.9 Hz), 7.52 (dd, 1H, J=8.5 and 1.9 Hz), 7.33 (m, 1H), 7.32 (d, 1H, 15.3 Hz), 7.01–7.06 (m, 2H), 6.82 (d, 1H, 7.9 Hz), 3.12 (m, 4H), 1.84 (m, 4H). MS m/z=403 ([M]+, 100%). HRMS (EI) Calcd. for C24H21NO3S: 403.1242. Found: 403.1251.

後処理

  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. customSilica gel chromatography (100% ethyl acetate) followed by recrystallization from ethanol

出典と根拠

ORDレコード
ord-3710f1d466844c3a80b01c2a0dd8ec27
出典データセット
uspto-grants-2006_08
特許番号
US07094801B2

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