Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | HCID 58026844 | HCID 58026844 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 58027060 | HCID 58027060 | 50% |
Reaction Steps
5-Hydroxymethyl-6-(2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 4-1, 2.00 g, 6.46 mmol) was dissolved in anhydrous dichloromethane (32 mL) and then triethylamine (1.35 mL, 9.69 mmol) and methanesulfonyl chloride (55 μL, 7.11 mmol) were added thereto at 0° C. The reaction mixturer was stirred at room temperature overnight. Ethyl acetate (500 mL), water (200 mL), and saturated brine (200 mL) were added to the reaction mixture and separated. The water layer was extracted with ethyl acetate (150 mL) and the organic layer was combined. The organic layer was washed with saturated brine (200 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (1.07 g) as a pale yellow solid. (Yield 50%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08420635B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-2bceeca33f284934afe1c576a1df371d |
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| Source note | uspto-grants-2013_04 |
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