Epichlorohydrin → HCID 86606985, compound

HRID 1868583Notes

Reaction equation

HRID 1868583 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][CH:17]=[C:16]([OH:23])[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][CH:17]=[C:16]([O:23][CH2:37][CH:39]1[O:41][CH2:40]1)[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 10575539HCID 10575539, compound2×

Product 1

HCID 86606985HCID 86606985, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Reaction of 3′,4′-dibenzyloxy-7-hydroxy-flavone, 23 (10 g, 22.2 mmol), 50% sodium hydride (3 g, 125 mmol) and epichlorohydrin (6.9 mL, 88 mmol) in dry dimethyl formamide (160 mL) using identical procedure as described for 28 furnished 29. Yield 9.7 g (86%); mp 168-170° C.; MS (FAB) 507 (M++1); IR (KBr) 1639; 1H NMR (200 MHz, CDCl3) δ 8.12 (d, J=8.7 Hz, 1H), 7.50-7.32 (m, 12H), 7.04-6.93 (m, 3H), 6.61 (s, 1H), 5.24 (s, 4H), 4.38 (dd, J=11.1 Hz, 2.9 Hz, 1H), 4.05 (dd, J=11.1 Hz, 5.8 Hz, 1H), 3.42-3.40 (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-45ad1a1e59924f18898d4779964ff283
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

Loading…