Methyl iodide → 1,3-Benzoxathiol-2-one, 5-methoxy-

HRID 1696713

Reaction equation

HRID 1696713 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[O:12])[S:9][C:8]=2[CH:13]=1.[CH3:14]I.[Cl-].[NH4+]>COCCOC>[CH3:14][O:3][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[O:12])[S:9][C:8]=2[CH:13]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1390671,3-Benzoxathiol-2-one, 5-hydroxy-

Product 1

HCID 1370241,3-Benzoxathiol-2-one, 5-methoxy-Yield 72%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

With cooling with ice, 60% oily sodium hydride (3.14 g) was added to a 1,2-dimethoxyethane (100 mL) solution of 5-hydroxy-1,3-benzoxathiol-2-one (10 g, 59.5 mmol), and stirred for 10 minutes. With cooling with ice, methyl iodide (37 mL) was added to the reaction liquid, and stirred for 2 hours with cooling with ice and further for 6 hours at room temperature. Aqueous saturated ammonium chloride solution was added to the reaction liquid, and extracted three times with chloroform. The organic layer was dried with magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/2) to obtain the intended compound (7.8 g, 72%) as a white solid.

Workup

  1. additionwas added to the reaction liquid
  2. stirringstirred for 2 hours
  3. extractionextracted three times with chloroform
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-21f2709b85934c2cbf5379274f00ed67
Source dataset
uspto-grants-2012_04
Patent number
US08163770B2

Linked notes

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