Water → HCID 53668106, compound

Participants

Reaction Conditions

Reaction Steps

5,6-Dichloronicotinic acid (1.92 g, 10.0 mmol) was slurried in 10 mL tetrahydrofuran to which carbonyldiimidazole (CDI) (1.78 g, 11.0 mmol) was added. The mixture was stirred at 40° C. for one hour to a uniform solution. 2-Methyl-3-butyn-2-ol (1.01 g, 12.0 mmol) was added via pipette and the solution refluxed overnight. The solution was poured into 4-5 volumes of water and extracted with Et2O (2×100 mL). The organics were washed with 2.0 N NaOH, dried over MgSO4, and concentrated to 1.2 g pale yellow oil. Crude product was chromatographed on medium column using silica gel (23-400 mesh) with descending solvent gradient from 100% petroleum ether to 50/50 pet. ether/ethyl acetate as the mobile phase. Elution and concentration gave (dimethyl)propargyl 5,6-dichloronicotinate (0.50 g) as a colorless oil.

Provenance & Evidence