Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | Ethyl 5-chloro-6-(1,1-difluoroethyl)nicotinate | HCID 86730206 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 86730205 | HCID 86730205 | 95.1% |
Reaction Steps
To a solution of ethyl 5-chloro-6-(1,1-difluoroethyl)nicotinate (2.68 g, 10.74 mmol) in Et2O (40 mL) was added LiBH4 (0.351 g, 16.10 mmol), followed by dropwise addition of methanol (0.653 mL, 16.10 mmol). The reaction was refluxed at 40° C. for one hour. The reaction mixture was then cooled to 0° C., and quenched with HCl (1M) until pH=2 for aqueous layer. The phases were separated and the aqueous layer was extracted with DCM (3×50 mL). The organic was then dried (Na2SO4) and concentrated under reduced pressure to give final crude product (2.12 g). LCMS m/z 208.0 (M+H)+, Rt 0.63 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09434719B2 |
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| Source dataset | uspto-grants-2016_09 |
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| ORD ID | ord-ec68920441b04f92af4b5a87376574ac |
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| Source note | uspto-grants-2016_09 |
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