Dimethyl Sulfate → HCID 59625722, compound

HRID 1911208Notes

Reaction equation

HRID 1911208 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-96be06f337bd44a5a8b065b876341dce
Source dataset
uspto-grants-2013_12
Patent number
US08604017B2

Reaction notes

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