Epichlorohydrin → HCID 86236608, compound

HRID 1868586Notes

Reaction equation

HRID 1868586 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1)[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+].[CH2:25]([CH:27]1[O:29][CH2:28]1)Cl>CN(C)C=O>[CH3:22][O:21][C:19]1[CH:18]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[CH:20]=1)[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[C:10]([O:17][CH2:25][CH:27]1[O:29][CH2:28]1)[CH:9]=2

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 69030367HCID 69030367, compound2×

Product 1

HCID 86236608HCID 86236608, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Reaction of 3′,5′-dimethoxy-7-hydroxy-flavone, 26 (2 g, 6.7 mol), 50% sodium hydride (0.96 g, 40 mmol) and epichlorohydrin (1.6 mL, 20 mmol) in dry dimethyl formamide (90 mL) using identical procedure as described for 28 furnished 32. Yield 1.7 g (72%); mp 181-182° C.; MS (FAB) 355 (M++1); IR (KBr) 1630; 1H NMR (200 MHz, CDCl3) δ 8.14 (dd, J=8.3 Hz, 0.77 Hz, 1H), 7.04-6.99 (m, 4H), 6.73 (s, 1H), 6.61 (t of dd, J=2.2 Hz, 2.2 Hz, 2.2 Hz, 1H), 4.39 (dd, J=11.1 Hz, 2.9 Hz, 1H), 4.06 (dd, J=11.1 Hz, 5.8 Hz, 1H), 3.87 (s, 6H), 3.44-3.39 (m, 1H), 2.96 (t, J=4.5 Hz, 4.5 Hz, 1H), 2.80 (dd, J=4.8 Hz, 2.6 Hz, 1H).

Sources & evidence

ORD record
ord-b69922d0e26543cc9593219b104b609c
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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