Epichlorohydrin → HCID 86236611, compound

HRID 1868587Notes

Reaction equation

HRID 1868587 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][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+].[CH2:25]([CH:27]1[O:29][CH2:28]1)Cl>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][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]([O:17][CH2:25][CH:27]1[O:29][CH2:28]1)[CH:9]=2

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 53785182-(3,4-Dimethoxyphenyl)-7-hydroxy-4H-chromen-4-one2×

Product 1

HCID 86236611HCID 86236611, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Reaction of 3′,4′-dimethoxy-7-hydroxy-flavone, 27 (6 g, 20 mol), 50% sodium hydride (2.4 g, 100 mmol) and epichlorohydrin (3.9 mL, 50 mmol) in dry dimethyl formamide (200 mL) using identical procedure as described for 28 furnished 33. Yield 5.3 g (74%); mp 148-149° C.; MS (FAB) 355 (M++1); IR (KBr) 1632; 1H NMR (200 MHz, CDCl3) δ 8.13 (d, J=9.5 Hz, 1H), 7.73 (dd, J=8.5 Hz, 2.0 Hz, 1H), 7.35 (d, J=1.9 Hz, 1H), 7.00 (dd, J=7.1 Hz, 2.3 Hz, 1H), 6.99 (d, J=2.2 Hz, 1H), 6.97 (d, J=8.5 Hz, 1H), 6.68 (s, 1H), 4.39 (dd, J=11.1 Hz, 2.9 Hz, 1H), 4.05 (dd, J=11.1 Hz, 5.8 Hz, 1H), 3.98 (s, 3H), 3.96 (s, 3H), 3.44-3.40 (m, 1H), 2.96 (t, J=4.5 Hz, 4.5 Hz, 1H), 2.81 (dd, J=4.8 Hz, 2.6 Hz, 1H).

Sources & evidence

ORD record
ord-96a4c0c9beb448eab5773adc6c0cb0dd
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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