HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetyl chloride → 1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridin-1(2H)-yl)ethan-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,2,3,6-Tetrahydropyridine-4-boronic acid, pinacol ester hydrochloride | HCID 49761084 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridin-1(2H)-yl)ethan-1-one | HCID 56737678 | 108% |
Reaction Steps
To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride (2.9 g, 11.8 mmol) in DCM (30 mL) were added Et3N (3.6 g, 35.4 mmol) and acetyl chloride (AcCl) (932 mg, 11.8 mmol). The reaction mixture was stirred at room temperature for 1 hour, then diluted with DCM (20 mL), washed with H2O (2.0 mL). The organic layer was washed with brine (20 mL), dried over Na2SO4, and filtered, evaporated to give the crude product (3.2 g, crude). ESI-MS (M+1): 252 calc. for C13H22BNO3 251.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08497265B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-b14a8dd6fb85405eab000bd592774e7d |
| Source note | uspto-grants-2013_07 |