Epichlorohydrin → HCID 86606987, compound

HRID 1868585Notes

Reaction equation

HRID 1868585 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[C:10]([OH:17])[CH:9]=2.[H-].[Na+].[CH2:27]([CH:29]1[O:31][CH2:30]1)Cl>CN(C)C=O>[O:31]1[CH2:30][CH:29]1[CH2:27][O:17][C:10]1[CH:9]=[C:8]2[C:13]([C:14](=[O:16])[CH:15]=[C:6]([C:5]3[CH:18]=[C:19]([O:23][CH3:24])[C:20]([O:21][CH3:22])=[C:3]([O:2][CH3:1])[CH:4]=3)[O:7]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 53819207-Hydroxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one2×

Product 1

HCID 86606987HCID 86606987, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Reaction of 3′,4′,5′-trimethoxy-7-hydroxy-flavone, 25 (8.2 g, 25 mol), 50% sodium hydride (3 g, 125 mmol) and epichlorohydrin (7.8 mL, 100 mmol) in dry dimethyl formamide (145 mL) using identical procedure as described for 28 furnished 31. Yield 8 g (83%); mp 187-188° C.; MS (FAB) 385 (M++1); IR (KBr) 1651; 1H NMR (200 MHz, CDCl3) δ 8.14 (d, J=9.3 Hz, 1H), 7.10 (s, 2H), 7.02 (d, J=7.6 Hz, 1H), 7.00 (s, 1H), 6.70 (s, 1H), 4.39 (dd, J=11.0 Hz, 2.8 Hz, 1H), 3.98 (dd, J=11.0 Hz, 5.7 Hz, 1H), 3.43-3.39 (m, 1H), 3.96 (s, 6H), 3.93 (s, 3H), 2.97 (t, J=4.5 Hz, 4.2 Hz, 1H), 2.82 (dd, J=4.7 Hz, 2.2 Hz, 1H).

Sources & evidence

ORD record
ord-71251eba5690476b9865ecc79ae07867
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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