Dimethyl Sulfate → HCID 66777635, compound

HRID 2091426Notes

Reaction equation

HRID 2091426 reaction equation
[CH:1]1([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:12]=3[C:13]=2[OH:14])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].S(OC)(O[CH3:26])(=O)=O>O1CCCC1.CN(C)C=O>[CH:1]1([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:12]=3[C:13]=2[O:14][CH3:26])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 66778296HCID 66778296, compound2×

Product 1

HCID 66777635HCID 66777635, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cyclohexyl(5-fluoro-3-hydroxy-1-benzofuran-2-yl)methanone (3.0 g) synthesized in the above-mentioned (1) was dissolved in tetrahydrofuran (15 mL) and N,N-dimethylformamide (15 mL). The reaction mixture was ice-cooled, sodium hydride (0.69 mg) was added to the solution, and the mixture was stirred for 15 min. Dimethyl sulfate (1.6 mL) was added to the mixture, and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the precipitate was recrystallized from diisopropyl ether-hexane to give the title object compound (2.0 g, 63%) as a colorless solid.

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred at room temperature overnight
  3. customThe solvent was evaporated under reduced pressure, water
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. concentrationThe extract was concentrated under reduced pressure
  7. customthe precipitate was recrystallized from diisopropyl ether-hexane

Sources & evidence

ORD record
ord-062551879b4d4188a5595bb6f3e0553a
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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