Imidazole → 3(2H)-Isoflavene

HRID 603286Notes

Reaction equation

HRID 603286 reaction equation
N1C=CN=C1.C(O[C:10]1[CH:30]=[CH:29][C:13]([C:14]2[CH2:15][O:16][C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[C:19](OC(=O)C)[C:18]=3C)=[CH:12][CH:11]=1)(=O)C>C(O)C>[O:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[C:14]([C:13]2[CH:29]=[CH:30][CH:10]=[CH:11][CH:12]=2)[CH2:15]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 9862674HCID 9862674, compound

Product 1

HCID 5004603(2H)-Isoflavene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Imidazole (0.6 g) was added to a suspension of 4′,7-diacetoxy-8-methylisoflav-3-ene (0.25 g, 0.7 mmol) in absolute ethanol (5.0 ml) and the mixture was refluxed for 45 min 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 8-methylisoflav-3-ene-4′,7-diol (0.13 g, 68%). m.p. 190-93° C. 1H NMR (CDCl3+d6-DMSO): δ 1.94 (s, 3H, CH3), 4.98 (s, 2H, H2), 6.32 (d, 1H, J 7.9 Hz, H6), 6.58 (bs, 1H, H4), 6.67 (bd, 1H, H5), 6.72 (d, 2H, J 8.7 Hz, ArH), 7.21 (bd, 2H, ArH). Mass spectrum: m/z 255 (M+1, 16%); 254 (M, 79); 253 (100); 161 (32).

Workup

  1. temperaturethe mixture was refluxed for 45 min 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-33e30f9c6cf04b53adcb83242f54dff1
Source dataset
uspto-grants-2011_03
Patent number
US07906660B2

Reaction notes

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