Methyl iodide → Methyl (4-oxo-4,10-dihydro-9-oxa-3-thiabenzo[f]azulen-6-ylsulfanyl)acetate
Reaction equation
CI.[C:3](=O)([O-])O.[K+].[O:8]=[C:9]1[C:18]2[CH:19]=[C:20]([S:23][CH2:24][C:25]([OH:27])=[O:26])[CH:21]=[CH:22][C:17]=2[O:16][CH2:15][C:14]2[CH:13]=[CH:12][S:11][C:10]1=2>CN(C=O)C>[O:8]=[C:9]1[C:18]2[CH:19]=[C:20]([S:23][CH2:24][C:25]([O:27][CH3:3])=[O:26])[CH:21]=[CH:22][C:17]=2[O:16][CH2:15][C:14]2[CH:13]=[CH:12][S:11][C:10]1=2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl iodide (6.5 mL, 104 mmol) and potassium hydrogencarbonate (17.0 g, 170 mmol) were added to a DMF (200 mL) solution of the compound obtained in Example 21 (26.1 g, 85 mmol), and the mixture was stirred at room temperature overnight. The solvents were distilled off under a reduced pressure, water was added to the residue, and the product was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution and then dried over anhydrous sodium sulfate, and the solvents were distilled off under a reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1), to give 24.0 g (88%) of the captioned compound.
Workup
- distillationThe solvents were distilled off under a reduced pressure, water
- additionwas added to the residue
- extractionthe product was extracted with ethyl acetate
- washThe organic layer was washed with a saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- distillationthe solvents were distilled off under a reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)
Sources & evidence
- ORD record
- ord-9da0e7f55a5e4a94b37ee17d1e2aa756
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08377967B2
Reaction notes
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