Imidazole → 2H-1-Benzopyran-7-ol, 3-phenyl-

HRID 603283Notes

Reaction equation

HRID 603283 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11][O:12]2)=[CH:7][CH:6]=1)(=O)C.N1C=CN=C1.O1C2C(=CC=C(O)C=2)C=C(C2C=CC(O)=CC=2)C1>C(O)C>[O:12]1[C:13]2[C:8](=[CH:7][CH:6]=[C:5]([OH:4])[CH:14]=2)[CH:9]=[C:10]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:11]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 219100PhenoxodiolHCID 54183938HCID 54183938, compound

Product 1

HCID 99426452H-1-Benzopyran-7-ol, 3-phenyl-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Isoflav-3-ene-7-ol was prepared from 7-acetoxyisoflav-3-ene (0.2 g, 0.75 mmol) and imidazole (0.24 g) in ethanol (3.5 ml) as described for isoflav-3-ene-4′,7-diol. Yield: (0.11 g, 66%) m.p. 120° C. 1H NMR (d6-DMSO): δ 5.07 (s, 2H, H2), 6.24 (d, 1H, J 2.2 Hz, H8), 6.33 (dd, 1H, J 1.9 Hz, 7.9 Hz, H6), 6.96 (d, 1H, J 7.9 Hz, H5), 7.00 (s, 1H, H4), 7.26-7.47 (m, 5H, ArH), 9.65 (bs, 1H, OH). Mass spectrum: m/z 224 (m, 74%); 223 (100), 175 (28); 165 (23); 147 (41).

Sources & evidence

ORD record
ord-7cfd7e423b0b41ee84b4c03f548be02d
Source dataset
uspto-grants-2011_03
Patent number
US07906660B2

Reaction notes

Loading…