Water → HCID 117701507, compound

HRID 1507456Notes

Reaction equation

HRID 1507456 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[OH:9][C:10]1[C:19]2[C:14](=[C:15]([CH3:24])[C:16]([O:20][CH2:21][O:22][CH3:23])=[CH:17][CH:18]=2)[O:13][C:12](=[S:25])[C:11]=1[CH3:26].O>CC(C)=O>[CH3:23][O:22][CH2:21][O:20][C:16]1[C:15]([CH3:24])=[C:14]2[C:19]([C:10](=[O:9])[C:11]([CH3:26])=[C:12]([S:25][CH3:1])[O:13]2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178497301HCID 178497301, compound

Product 1

HCID 117701507HCID 117701507, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (995 mg, 7.20 mmol) and methyl iodide (1.50 mL, 24.0 mmol) were added to a solution of 4-hydroxy-7-(methoxymethoxy)-3,8-dimethyl-2H-chromene-2-thione (1.60 g, 6.00 mmol) obtained in Example 37-1 in acetone (16 mL), and the mixture was refluxed for 45 minutes. After cooling to room temperature, water (15 mL) was added to the reaction solution, followed by extraction with ethyl acetate. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=95/5→60/40) to obtain 1.34 g of the title compound (yield: 80%).

Workup

  1. temperaturethe mixture was refluxed for 45 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=95/5→60/40)

Sources & evidence

ORD record
ord-81391011c7164d59824e31f293f2dcc1
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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