Ethanol → 4-[(3-Ethyloxetan-3-yl)methoxy]aniline

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-ethyl-3-((4-nitrophenoxy)methyl)oxetane (8.28 g, 34.9 mmol) in a 3:3:1 mixture of THF:EtOH:water (140 mL) at room temperature was added ammonium chloride (2.80 g, 52.3 mmol) followed by iron powder (9.74 g, 174 mmol). The mixture was heated to 90° C. for 1 hour, then it was filtered hot through diatomaceous earth with a THF wash to complete the transfer. The filtrate was concentrated under reduced pressure, and the residue was taken up in ethyl acetate then washed with brine, dried (Na2SO4), and concentrated to provide the title compound (7.12 g, 98% yield) without further purification.

Provenance & Evidence