Water → HCID 23158226, compound

HRID 601656Notes

Reaction equation

HRID 601656 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+].[CH3:22]I.O>CN(C)C=O>[CH3:22][CH:11]1[CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([O:12][S:13]([C:16]([F:19])([F:17])[F:18])(=[O:15])=[O:14])[CH:5]=[CH:4][C:3]=2[C:2]1=[O:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 110983845-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 23158226HCID 23158226, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under nitrogen atmosphere, 200 mg of trifluoromethanesulfonate 5-oxo-5,6,7,8-tetrahydro-naphthalene-2-ylester was dissolved in 3 ml of dimethylformamide. 54 mg of 60% sodium hydroxide and 1.0 ml of methyl iodide were added and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution, extracted with ethyl acetate. Ethyl acetate layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. The solvents were distilled outunder reduced pressure, and the residues were separated and purified by preparative thin-layer chromatography (ethyl acetate/hexane=1/2) to obtain 42 mg of the above compound as a yellow oily matter.

Workup

  1. extractionextracted with ethyl acetate
  2. washEthyl acetate layer was washed with saturated saline solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationThe solvents were distilled outunder reduced pressure
  5. customthe residues were separated
  6. custompurified by preparative thin-layer chromatography (ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-e3bb9e32c691460eb5b5b43665c7646a
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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