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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 454891Generated: October 30, 2026

Acetyl chloride → 1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridin-1(2H)-yl)ethan-1-one

https://huagongshe.com/reaction/454891

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetyl chlorideHCID 6367—
ReactantTriethylamineHCID 8471—
Reactant1,2,3,6-Tetrahydropyridine-4-boronic acid, pinacol ester hydrochlorideHCID 49761084—
SolventDichloromethaneHCID 6344—
Product1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridin-1(2H)-yl)ethan-1-oneHCID 56737678108%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08497265B2
Source datasetuspto-grants-2013_07
ORD IDord-b14a8dd6fb85405eab000bd592774e7d
Source noteuspto-grants-2013_07