Iodoethane → HCID 70560825, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2b (10.0 g, 24.1 mmol) in DMF (20 mL) was added via syringe pump (1.6 mL/min) to a stirred suspension of sodium hydride (964 mg of a 60% wt/wt dispersion in mineral oil, 24.1 mmol) in DMF (60 mL) at 0° C. After 15 min, iodoethane (2.34 mL, 28.9 mmol) was added rapidly dropwise, and the resulting mixture was stirred at 0° C. for 2 h. The reaction was quenched by addition of saturated aqueous ammonium chloride and extracted with ether. The combined organics were washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo. The resulting crude oil was purified by flash chromatography on silica gel (gradient elution; 0%-20% EtOAc/hexanes as eluent) to afford the title compound 3a. m/z (ES) 465 (MNa)+.

Provenance & Evidence