Epichlorohydrin → HCID 86606986, compound

HRID 1868584Notes

Reaction equation

HRID 1868584 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[CH:18][C:17]([OH:23])=[CH:16][CH:15]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:37]([CH:39]1[O:41][CH2:40]1)Cl>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[CH:18][C:17]([O:23][CH2:37][CH:39]1[O:41][CH2:40]1)=[CH:16][CH:15]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 69030375HCID 69030375, compound2×

Product 1

HCID 86606986HCID 86606986, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Reaction of 3′,4′-dibenzyloxy-6-hydroxy-flavone, 24 (4.5 g, 10 mmol), 50% sodium hydride (1.4 g, 60 mmol) and epichlorohydrin (4.7 mL, 60 mmol) in dry dimethyl formamide (120 mL) using identical procedure as described for 28 furnished 30. Yield 4.2 g (81%); mp 147-149° C.; MS (FAB) 507 (M++1); IR (KBr) 1610; 1H NMR (200 MHz, CDCl3) δ 7.57-7.29 (m, 15H), 7.02 (d, J=8.6 Hz, 1H), 6.66 (s, 1H), 5.25 (s, 4H), 4.39 (dd, J=11.0 Hz, 2.6 Hz, 11H), 3.98 (dd, J=11.0 Hz, 6.0 Hz, 1H), 3.40-3.39 (m, 1H), 2.93 (t, J=4.5 Hz, 4.5 Hz 1H), 2.78 (dd, J=4.8 Hz, 2.6 Hz, 1H).

Sources & evidence

ORD record
ord-cd99ee61ed9b4c42bf5b88f8743db731
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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