Iodoethane → HCID 23525787, compound

Participants

Reaction Steps

To a suspension of sodium hydride (477 mg, 18.88 mmol) (Aldrich, 95%) in tetrahydrofuran (25 mL) was added a solution of [3-(4-nitrophenoxy)propyl]-carbamic acid tert-butyl ester (3.0 g, 10.13 mmol) (from Example 64, Step A) in tetrahydrofuran (15 mL) at 0° C. Upon addition, the mixture was allowed to stir at room temperature for 30 minute, treated with iodoethane (3.76 g, 24.25 mmol) (Aldrich), and heated at 55° C. for one hour before it was quenched with aqueous ammonium chloride (20 mL). The resulting mixture was extracted with ethyl acetate (3×100 mL) and the combined organic extracts were washed with brine and dried (Na2SO4) and evaporated in vacuo. The residue was purified on silica gel with 75:25 hexane/ethyl acetate to give ethyl-[3-(4-nitrophenoxy) propyl]carbamic acid tert-butyl ester (3.15 g, 96%). MS (ES) MH+=325.

Provenance & Evidence