Imidazole → HCID 54121012, compound

HRID 603292Notes

Reaction equation

HRID 603292 reaction equation
C([O:4][C:5]1[C:14]([CH3:15])=[C:13]2[C:8]([C@@H:9]([OH:24])[C@H: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>C(O)C>[OH:4][C:5]1[C:14]([CH3:15])=[C:13]2[C:8]([C@@H:9]([OH:24])[C@H: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

Participants

4

Reactant 2

HCID 795ImidazoleHCID 54563226HCID 54563226, compound

Product 1

HCID 54121012HCID 54121012, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

trans-7-Hydroxy-4′-methoxy-8-methylisoflavan-4-ol was prepared from trans-7-acetoxy-4′-methoxy-8-methylisoflavan-4-ol (0.23 g, 0.7 mmol) and imidazole (0.28 g) in ethanol (2.1 ml) as described for cis- and trans-tetrahydrodaidzein. m.p. 162° C. Mass spectrum: 285 M, 5%); 268 (10); 151 (20); 135 (20); 134 (100); 119 (20). 1H NMR (d6-acetone): δ 1.97 (s, 3H, CH3), 3.00 (ddd, 1H, J 3.4 Hz, 7.2 Hz, 10.2 Hz, H3), 3.72 (s, 3H, OMe), 4.20 (dd, 1H J 7.5 Hz, 10.9 Hz, H2); 4.27 (m, 1H, H2), 4.73 (d, 1H, J 6.8 Hz, H4), 6.45 (d, 1H, J 8.3 Hz, H6), 6.85 (d, 2H, J 8.6 Hz, ArH), 7.10 (d, 1H, J 8.7 Hz, H5), 7.18 (d, 2H, J 8.6 Hz, ArH).

Sources & evidence

ORD record
ord-848218a86b614cf79a9f63a14d0ea0b7
Source dataset
uspto-grants-2011_03
Patent number
US07906660B2

Reaction notes

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