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

HRID 10678

反応式

HRID 10678 の反応式
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[CH:6][C:3]=1[CH:4]=O.[C:17]([C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1)(=[O:19])[CH3:18].C[O-].[Li+].Cl>CN(C)C=O.CO.O>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[CH:6][C:3]=1/[CH:4]=[CH:18]/[C:17]([C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1)=[O:19]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 114704-Acetylbenzoic AcidHCID 4177230Lithium methanolateHCID 118589982-Hydroxy-4-methoxy-5-thiophen-2-yl-benzaldehyde

生成物 1

HCID 102158724-[3E-(2-Hydroxy-4-methoxy-5-thiophen-2-yl-phenyl)acryloyl]-benzoic acid収率 15.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21901440N,N-dimethylformamide methanol溶媒

実験手順

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.

後処理

  1. additionwas added
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. customevaporated to dryness
  5. temperaturewarmed to 60° C.
  6. customto obtain complete
  7. dissolutiondissolution
  8. temperatureto cool to room temperature
  9. temperaturewith heating
  10. customThe resulting precipitate was collected
  11. filtrationon filter paper
  12. customdried in vacuo

出典と根拠

ORDレコード
ord-a2abe984cff548c283fad39ead5f0743
出典データセット
uspto-grants-2006_08
特許番号
US07094801B2

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