1-Chloroethyl chloroformate → 4-Ethenyl-2,3-dihydro-1H-isoindole

Participants

Reaction Conditions

Reaction Steps

A solution of 1-chloroethyl chloroformate (7.51 mL, 69.6 mmol) in 1,2-dichloroethane was added to a cooled (ice bath) solution of 2-benzyl-4-vinylisoindoline (58 mmol) in 1,2-dichloroethane (150 mL) over 20 minutes, maintaining the internal reaction temperature<5° C. After addition was complete, the reaction mixture was allowed to warm to RT, then heated to reflux for 45 minutes. The reaction mixture was recooled to RT, and the solvent was removed by evaporation. MeOH (200 mL) was added, and the mixture was heated to reflux for 30 minutes, then cooled to RT. The solvent was then removed by evaporation. Water (200 mL) was added, and the resulting mixture was washed with EtOAc (2×250 mL). The aqueous layer was made basic with 2N sodium hydroxide then extracted with DCM (4×250 mL). The combined organic extracts were dried over Na2SO4 and filtered, and the solvent was evaporated. The crude product was purified by chromatography on silica (DCM/MeOH/NH4OH 97/3/0.3 to 95/5/0.5) to give the title compound as a brown oil, (6.00 g). LRMS (ESI) m/z 146 [(M+H)+; calcd for C10H12N: 146].

Provenance & Evidence