Imidazole → 3(2H)-Isoflavene

HRID 603280ノート

反応式

HRID 603280 の反応式
N1C=CN=C1.C(O[C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([C:20]3[CH:25]=[CH:24][C:23](OC)=[CH:22][CH:21]=3)[CH2:16][O:17]2)=[CH:12][CH:11]=1)(=O)C>C(O)C>[O:17]1[C:18]2[C:13](=[CH:12][CH:11]=[CH:10][CH:19]=2)[CH:14]=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16]1

参加物

4

反応物 2

HCID 795ImidazoleHCID 264550MLS002703491

生成物 1

HCID 5004603(2H)-Isoflavene

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Imidazole (0.18 g) was added to a suspension of 7-acetoxy-4′-methoxyisoflav-3-ene (0.06 g, 0.02 mmol) in absolute ethanol (5.0 ml) and the mixture was refluxed for 45 minutes under argon. The solution was concentrated under reduced pressure and the product was precipitated by addition of distilled water (10 ml). The mixture was left overnight in the fridge and filtered to yield isoflav-3-ene. The crude product was recrystallised from methanol/benzene to yield 7-hydroxy-4′-methoxyisoflav-3-ene (0.034 g, 66%). 1H NMR (CDCl3+d6-DMSO): δ 3.74 (s, 3H, OCH3), 4.99 (s, 2H, H2), 6.21 (d, 1H, J 2.3 Hz, H8), 6.29 (dd, 1H, J 2.3 Hz, 8.3 Hz, H6), 6.67 (bs, 1H, H4), 6.85 (d, 1H, J 8.3 Hz, H5), 6.86 (d, 2H, J 8.7 Hz, ArH), 7.33 (d, 2H, J 8.7 Hz, ArH).

後処理

  1. temperaturethe mixture was refluxed for 45 minutes under argon
  2. concentrationThe solution was concentrated under reduced pressure
  3. customthe product was precipitated by addition of distilled water (10 ml)
  4. filtrationfiltered

出典と根拠

ORDレコード
ord-107dd5d8e21a43ffad44953eab33cd2c
出典データセット
uspto-grants-2011_03
特許番号
US07906660B2

反応ノート

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