Dimethyldioxirane → 5,7-Bis-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one

HRID 1821062Notes

Reaction equation

HRID 1821062 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:16]=[C:15]2[C:10]=1[C:11](=[O:41])[CH:12]=[C:13]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:29][CH:28]=1)[O:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)O[O:44]1>C(Cl)Cl.CC(C)=O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:16]=[C:15]2[C:10]=1[C:11](=[O:41])[C:12]([OH:44])=[C:13]([C:27]1[CH:28]=[CH:29][C:30]([O:33][CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[CH:31][CH:32]=1)[O:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 115197DimethyldioxiraneHCID 11180247MLS000517991

Product 1

HCID 112729065,7-Bis-(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution containing 1.00 g (1.85 mmol) of 3 in 30 mL of CH2Cl2 at 0° C. was added 30 mL of a 0.9-0.11 M solution of DMDO in acetone. The reaction mixture was stirred at 0° C. overnight under N2.

Sources & evidence

ORD record
ord-28f49aa3149243459ef6157db69de254
Source dataset
uspto-grants-2009_10
Patent number
US07605241B2

Reaction notes

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