2,3-Dichloropropene → HCID 86665069, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl cyclopentanecarboxylate (2.0 g, 15.60 mmol) in THF (70 mL) cooled to −78° C. was added 2 M solution of LDA in THF (10.1 mL, 20.3 mmol). The mixture was stirred at −78° C. for 1 hour. To this mixture was added 2,3-dichloroprop-1-ene (3.46 g, 31.2 mmol) and allowed to warm to room temperature. The reaction mixture was quenched with aq. NH4Cl and extracted with EtOAc. The organic layer was washed with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by chromatography using EtOAc/heptane gradient to give methyl 1-(2 chloroallyl)cyclopentanecarboxylate (1.82 g). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.46-1.75 (m, 6H), 1.98-2.18 (m, 2H), 2.66 (s, 2H), 3.61 (s, 3H), 5.02 (d, J=1.3 Hz, 1H), 5.14 (d, J=1.3 Hz, 1H).

Provenance & Evidence