HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 2-(5-Bromopyridin-3-yl)ethan-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 2-(5-Bromopyridin-3-yl)acetic acid | HCID 2802539 | — |
| Reactant | Diborane tetrahydrofuran | HCID 131714434 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 2-(5-Bromopyridin-3-yl)ethan-1-ol | HCID 53403690 | 23.9% |
Reaction Steps
A solution of Diborane-THF complex (1.0 M in THF, 7.5 mL, 7.5 mmol) was added dropwise to a solution of 5-bromo-3-pyridinylacetic acid (1080 mg, 5 mmol) in dry THF at 0° C. The resulting mixture was allowed to warm to room temperature. After 15 h, the reaction mixture was cooled to 0° C. and water (10 mL) was added dropwise. The reaction mixture was diluted with ethyl acetate (100 mL). The organic layer was separated, washed with brine, dried over Na2SO4. After filtration and concentration, the residue was purified by flash column and afforded of the title compound as colorless solid (241 mg). 1HNMR (CDCl3, 400.342 MHz) δ 2.89 (t, J=6 Hz, 2H), 3.92 (t, J=6 Hz, 3H), 7.99 (s, 1H), 8.46 (s, 1H), 8.60 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08455522B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-c1b90bd9127a4706905ad6980b1cac65 |
| Source note | uspto-grants-2013_06 |