Imidazole → 3(2H)-Isoflavene

HRID 603280Notes

Reaction equation

HRID 603280 reaction equation
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

Participants

4

Reactant 2

HCID 795ImidazoleHCID 264550MLS002703491

Product 1

HCID 5004603(2H)-Isoflavene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-107dd5d8e21a43ffad44953eab33cd2c
Source dataset
uspto-grants-2011_03
Patent number
US07906660B2

Reaction notes

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