Dimethylformamide → 1-hydroxy-3-(oxiran-2-ylmethoxy)-12H-benzo[b]xanthen-12-one

HRID 83109

Reaction equation

HRID 83109 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[C:11]4[CH:17]=[CH:18][CH:19]=[CH:20][C:10]4=[CH:9][C:8]=3[O:7][C:6]=2[CH:5]=[C:4]([OH:21])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C.[CH2:33]([CH:35]1[O:37][CH2:36]1)Cl>O>[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[C:11]4[CH:17]=[CH:18][CH:19]=[CH:20][C:10]4=[CH:9][C:8]=3[O:7][C:6]=2[CH:5]=[C:4]([O:21][CH2:33][CH:35]2[CH2:36][O:37]2)[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 107077051,3-dihydroxy-12H-benzo(b)xanthen-12-one

Product 1

HCID 462326461-hydroxy-3-(oxiran-2-ylmethoxy)-12H-benzo[b]xanthen-12-oneYield 10.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,3-dihydroxy-12H-benzo[b]xanthen-12-one (0.1 g, 0.36 mmol) synthesized in Step 1 of Example 18, K2CO3 (0.2 g, 1.44 mmol), and DMF (5 mL) were added to a dry round-bottom flask, and epichlorohydrin (0.19 g, 2.16 mmol) was added thereto with stirring using a syringe. The reaction mixture was stirred under a nitrogen atmosphere (75° C., overnight). After the reaction was completed, water was added to the reaction mixture which was then extracted twice with ethyl acetate. The organic layer was combined, washed with brine and dried over anhydrous Na2SO4. This liquid was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v)) to give the title compound (13 mg, 10.8%) as a yellow solid.

Workup

  1. stirringThe reaction mixture was stirred under a nitrogen atmosphere (75° C., overnight)
  2. extractionwas then extracted twice with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationThis liquid was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was separated
  8. custompurified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:3 (v/v))

Sources & evidence

ORD record
ord-5b10a7674ef2473ab6300333901e8b9f
Source dataset
uspto-grants-2014_09
Patent number
US08846749B2

Linked notes

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