Dimethyl Sulfate → HCID 59625722, compound

HRID 2365376Notes

Reaction equation

HRID 2365376 reaction equation
[OH:1][C:2]1[C:3]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].S(OC)(O[CH3:23])(=O)=O.C(=O)(O)[O-].[Na+]>CC(C)=O>[CH3:23][O:1][C:2]1[C:3]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 59625897HCID 59625897, compound

Product 1

HCID 59625722HCID 59625722, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of compound 68b (0.543 mmol, 150 mg), dimethyl sulfate (0.608 mmol, 0.058 mL), and sodium bicarbonate (0.57 mmol, 48 mg) in acetone was heated at reflux overnight. The reaction mixture was cooled and filtered. The filtrate was concentrated and the residue was partitioned between EtOAc and water. The organic solution was concentrated and purified by flash column chromatography (silica gel, 10% EtOAc/hexanes) to give compound 68c.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was partitioned between EtOAc and water
  7. concentrationThe organic solution was concentrated
  8. custompurified by flash column chromatography (silica gel, 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-eeb8514857884cdfa1d4e5a9057cd118
Source dataset
uspto-grants-2014_04
Patent number
US08697684B2

Reaction notes

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