Imidazole → HCID 10199252, compound

HRID 603288Notes

Reaction equation

HRID 603288 reaction equation
C([O:4][C:5]1[C:14]([CH3:15])=[C:13]2[C:8]([CH:9]=[C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH2:11][O:12]2)=[CH:7][CH:6]=1)(=O)C.N1C=CN=C1.CC1C(O)=CC=C2C=1OCC(C1C=CC(O)=CC=1)=C2>C(O)C>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:10]2[CH2:11][O:12][C:13]3[C:8]([CH:9]=2)=[CH:7][CH:6]=[C:5]([OH:4])[C:14]=3[CH3:15])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 9796709HCID 9796709, compoundHCID 10131253HCID 10131253, compound

Product 1

HCID 10199252HCID 10199252, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4′-Methoxy-8-methylisoflav-3-ene-7-ol was prepared from 7-acetoxy-4′-methoxy-8-methylisoflav-3-ene (0.11 g, 0.3 mmol) and imidazole (0.14 g) in ethanol (1.5 ml) as described for 8-methylisoflav-3-ene-4′,7-diol. Yield: (0.05 g, 53%) m.p. 103° C. 1H NMR (d6-acetone): δ 1.99 (s, 3H, CH3), 3.81 (s, 3H, OMe), 5.11 (s, 2H, H2), 6.43 (d, 1H, J 8.3 Hz, H6), 6.77 (bs, 1H, H4), 6.80 (d, 1H, J 8.3 Hz, H5), 6.95 (d, 2H, J 9.0 Hz, ArH), 7.44 (d, 2H, J 9.0 Hz, ArH). Mass spectrum: 282 (M, 9%); 267 (100); 268 (95); 134 (52).

Sources & evidence

ORD record
ord-c0b4e3f5d65341d29f4e5947c96aa795
Source dataset
uspto-grants-2011_03
Patent number
US07906660B2

Reaction notes

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