Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Chloromethyl Methyl Ether | HCID 7864 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methyl 6-bromo-3-hydroxypicolinate | HCID 22175135 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 86707002 | HCID 86707002 | 100% |
Reaction Steps
Diisopropylethylamine (1.46 mL) was added to a chloroform (20 mL) solution of methyl 6-bromo-3-hydroxypyridine-2-carboxylate (970 mg) and placed in a nitrogen atmosphere. Next, the reaction mixture was cooled to 0° C., and chloromethoxymethane (0.38 mL) was added thereto. The reaction mixture was stirred at 0° C. for 5 minutes, and then stirred at room temperature for 1 hour. The reaction mixture was cooled to 0° C., diluted with water, and extracted with chloroform. The combined organic layer was washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate) to give the desired product (1.22 g, yield: 100%) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09375434B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-2a57d0bca26e4c7b8826897ee681e267 |
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| Source note | uspto-grants-2016_06 |
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