Diethyl Ether → HCID 88920334, compound

HRID 1748993Notes

Reaction equation

HRID 1748993 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([CH:9]1[O:11][CH2:10]1)Cl.[OH:12][C:13]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([OH:24])[CH:20]=2)[O:15][C:14]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Cl-].[NH4+].[CH2:33]([O:35][CH2:36][CH3:37])C>O.CN(C=O)C>[O:11]1[CH2:10][CH:9]1[CH2:7][O:12][C:13]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH2:37][CH:36]3[CH2:33][O:35]3)[CH:20]=2)[O:15][C:14]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 5

HCID 3283Diethyl EtherHCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 6886593,6-Dihydroxyflavone

Product 1

HCID 88920334HCID 88920334, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

In a DMF (4 mL) solvent, potassium carbonate (180.2 mg, 1.30 mmol) and epichlorohydrin (0.2 mL, 2.17 mmol) were added to a 3,6-dihydroxyflavone (3,6-dihydroxyflavone) (110.5 mg, 0.43 mmol) solution. After stirring at a temperature of 70° C. for 8 hours, an ammonium chloride aqueous solution was added to the reaction mixture. The reaction mixture was distributed between diethyl ether and water, and an organic layer was dried by using anhydrous MgSO4, filtered, and evaporated under reduced pressure. The residual was purified by silica gel column chromatography using hexane and ethyl acetate (1:1.5) as a developer to obtain Compound 106 (25.3 mg, 16%) that is a white solid bis-oxyranyl flavone.

Workup

  1. customan organic layer was dried
  2. filtrationfiltered
  3. customevaporated under reduced pressure
  4. customThe residual was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c8769c614c694cbcaf7fa597f8119be4
Source dataset
uspto-grants-2015_10
Patent number
US09155690B2

Reaction notes

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