Diethyl Sulfate → HCID 69269049, compound

HRID 1795332Notes

Reaction equation

HRID 1795332 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][C:11]([OH:17])=[CH:10][C:9]=2[Br:18])=[O:5])[CH3:2].S(OCC)(O[CH2:23][CH3:24])(=O)=O.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][C:11]([O:17][CH2:23][CH3:24])=[CH:10][C:9]=2[Br:18])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6163Diethyl SulfateHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 69269182HCID 69269182, compound

Product 1

HCID 69269049HCID 69269049, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a 100 mL 3 neck round bottom flask equipped with a reflux condenser, nitrogen inlet and magnetic stirrer is added 700 mg (2.24 mg, 1.0 equiv.) of 8-Bromo-6-hydroxy-4-oxo-4H-chromene-carboxylic acid ethyl ester (Reference Example 23a). This material is dissolved in 50 mL of toluene, then 689 mg, 586 μL (4.47 mmol, 2.0.equiv.) of diethyl sulfate and 309 mg (2.24 mmol, 1.0 equiv.) of K2CO3 were added. The reaction was then heated to reflux for 24 hr. At the end of this time, monitoring by LC/MS reveals that the reaction is >than 95% complete. The reaction is then cooled, 100 mL of ethyl acetate is added and the organic layer is washed with 0.5N HCl solution, dried over Na2SO4, filtered and concentrated. The residues were subjected to flash chromatography, using 40% ethyl acetate in hexane as eluent. The purified fractions were concentrated to yield 500 mg (65%) of a colorless solid.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for 24 hr
  3. temperatureThe reaction is then cooled
  4. washthe organic layer is washed with 0.5N HCl solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. concentrationThe purified fractions were concentrated

Sources & evidence

ORD record
ord-8723c5a36eef4716a88b41d975f483f2
Source dataset
uspto-grants-2006_04
Patent number
US07026314B2

Reaction notes

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