Water → 6-Isopropoxy-1,3-benzoxathiol-2-one

HRID 1045327Notes

Reaction equation

HRID 1045327 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7](I)([CH3:9])[CH3:8].[OH:11][C:12]1[CH:21]=[CH:20][C:15]2[S:16][C:17](=[O:19])[O:18][C:14]=2[CH:13]=1.O>CN(C)C=O>[CH:7]([O:11][C:12]1[CH:21]=[CH:20][C:15]2[S:16][C:17](=[O:19])[O:18][C:14]=2[CH:13]=1)([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 721396-Hydroxy-1,3-benzoxathiol-2-one

Product 1

HCID 107984986-Isopropoxy-1,3-benzoxathiol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (829 mg) and isopropyl iodide (300 μL) were added to a solution of 6-hydroxy-1,3-benzoxathiol-2-one (504 mg) in N,N-dimethylformamide (15 mL) to form a reaction solution. This reaction solution was stirred for 4 hours at normal temperature, and then for 8 hours at 40° C. Water was added to the reaction solution, and the reaction solution was extracted with ethyl acetate. The extract was washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was removed by filtration, and then the solvent was removed by distillation under reduced pressure. The resultant product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain the target product (300 mg) as a colorless oil.

Workup

  1. customto form a reaction solution
  2. waitfor 8 hours at 40° C
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe anhydrous sodium sulfate was removed by filtration
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe resultant product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-19edcd5aab144c9c87cd0ba1b4b19bdb
Source dataset
uspto-grants-2013_10
Patent number
US08569270B2

Reaction notes

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