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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 412147Generated: October 28, 2026

Dimethylformamide → HCID 22943095, compound

https://huagongshe.com/reaction/412147

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantEthyl AcetateHCID 8857—
ReactantHCID 18536033HCID 18536033—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
CatalystHCID 178418397HCID 178418397—
ProductHCID 22943095HCID 22943095—

Reaction Conditions

Temperature80 °C

Reaction Steps

To a degassed solution of the triflate from Step A (40.92 g, 132.8 mmol) in 250 mL of DMF was added Zn(CN)2 (15.6 g, 132.8 mmol) and Pd(PPh3)4 (7.67 g, 6.64 mmol). The reaction was stirred at 80° C. for three days. Another portion of Zn(CN)2 (10 g) and Pd(PPh3)4 (5 g) was added the reaction was stirred at 80° C. for 24 hours, then cooled to room temperature. The solution was poured into EtOAc, washed with water, sat. aq. NaHCO3, and brine, then dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product. Purification by crystallization (10% EtOAc/hexane) provided the titled product as white needles.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06562823B1
Source datasetuspto-grants-2003_05
ORD IDord-b7c12ef7bea3465192ff70c67dfcc6d6
Source noteuspto-grants-2003_05