Hydrochloric Acid → Methyl (3-(2-methanesulfonyloxyethyl)benzofuran-7-yloxy)acetate
Reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:7]=2[O:6][CH:5]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].Cl>ClCCl>[CH3:26][S:27]([O:1][CH2:2][CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:7]=2[O:6][CH:5]=1)(=[O:29])=[O:28]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Methyl (3-(2-hydroxyethyl)benzofuran-7-yloxy)acetate (4.12 g) was dissolved in dichloromethane (120 ml) and triethylamine (3 ml) and methanesulfonyl chloride (1.35 ml) were added to the solution, followed by stirring the resulting solution at 0° C. for 1.5 hours. The reaction mixture was then poured into 1N hydrochloric acid and the resultant was extracted with dichloromethane. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution, water, and with saturated saline, and dried over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure. The residue was recrystallized from n-hexane/ethyl acetate to obtain the desired compound (5.25 g, yield: 97%).
Workup
- extractionthe resultant was extracted with dichloromethane
- washThe organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution, water
- dry with materialwith saturated saline, and dried over sodium sulfate
- customAfter removing the sodium sulfate
- filtrationby filtration
- customthe solvent was removed under reduced pressure
- customThe residue was recrystallized from n-hexane/ethyl acetate
Sources & evidence
- ORD record
- ord-548fb694717a44c78fb4457cbc5ff0c7
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06323235B1
Reaction notes
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