Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 71236655 | HCID 71236655 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 66825621 | HCID 66825621 | 35.4% |
Reaction Steps
To a solution of ethyl 2-(5-(4-chloro-3-(trifluoromethyl)phenoxy)pyridin-2-yl)acetate (2 g, 4.45 mmol) in ethanol (20 mL) was added sodium borohydride (1.683 g, 44.5 mmol). The reaction mixture was stirred at 20° C. for 10 hr. To the reaction mixture was added 50 mL of H2O and 50 mL of CH2Cl2. The organic layer was separated and dried over Na2SO4 and concentrated under reduced pressure. The crude product was added to a prep HPLC column eluting with MeCN/TFA 0.1% to provide 2-(5-(4-chloro-3-(trifluoromethyl)phenoxy)pyridin-2-yl)ethanol (500 mg, 25.5%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09273054B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-0c3200632afd4ffcb74e53fd10de8de0 |
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| Source note | uspto-grants-2016_03 |
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