Dimethyl Sulfate → HCID 19917146, compound

HRID 1464743Notes

Reaction equation

HRID 1464743 reaction equation
[CH2:1]([N:3]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]2[CH:35]=[CH:34][S:33][CH:32]=2)[CH:26]=1)[CH2:4]/[CH:5]=[CH:6]/[C:7]#[C:8][C:9]([C:15]([F:18])([F:17])[F:16])([OH:14])[C:10]([F:13])([F:12])[F:11])[CH3:2].[H-].[Na+].S(OC)(O[CH3:42])(=O)=O>CN(C)C=O>[CH2:1]([N:3]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]2[CH:35]=[CH:34][S:33][CH:32]=2)[CH:26]=1)[CH2:4]/[CH:5]=[CH:6]/[C:7]#[C:8][C:9]([C:15]([F:18])([F:17])[F:16])([O:14][CH3:42])[C:10]([F:11])([F:12])[F:13])[CH3:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 19916977HCID 19916977, compound

Product 1

HCID 19917146HCID 19917146, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

159 mg of (E)-ethyl-N-(7,7,7-trifluoro-6-trifluoromethyl-6-hydroxy-2-hepten-4-ynyl)-2-[2-[3-(3-thienyl)phenoxy]ethoxy]ethylamine was dissolved in 2 ml of dimethylformamide, and 24 mg of 60% oily sodium hydride was added. The mixture was stirred at room temperature for 10 minutes. To this solution was added 60 μl of dimethyl sulfate, and then the mixture was stirred at room temperature for 4 hours. The solvent was evaporated under reduced pressure, and ethyl acetate and water were added to the residue to extract it. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The desiccant was separated by filtration, and the solvent was evaporated. The residue was purified by silica gel column chromatography [methylene chloride/methanol=70/1] to give 24 mg (yield 15%) of the captioned compound as a pale yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. customThe solvent was evaporated under reduced pressure, and ethyl acetate and water
  3. additionwere added to the residue
  4. extractionto extract it
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe desiccant was separated by filtration
  9. customthe solvent was evaporated
  10. customThe residue was purified by silica gel column chromatography [methylene chloride/methanol=70/1]

Sources & evidence

ORD record
ord-b078623f5e494d7c8d46c635cb8f7de1
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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