Potassium Carbonate → HCID 69966543, compound

Participants

Reaction Steps

A solution of 1-[4-phenylmethoxy-3-nitrophenyl]propene (12.74 g, 47.3 mmol) and SnCl2.2H2O (53.4 g, 237 mmol) in 200 mL of EtOAc was refluxed for one hour. After cooling, 100 mL of hexane and then a solution of 41 g of K2CO3 (297 mmol) in 35 mL H2O were added with vigorous stirring, whereupon 300 mL of CH2Cl2 and 100 g Na2SO4 were added prior to filtration through Celite. After concentration, the residue was chromatographed twice on silica gel eluting with 7% to 17% Et2O/hexane to obtain 3.66 g of 1-[3-amino-4-phenylmethoxyphenyl]propene as a 98:2 mixture of trans to cis isomers. The title compound was prepared from 1-[3-amino-4-phenylmethoxyphenyl]propene following the procedure described in part 4 of step F of Example 1, except that the crude product was chromatographed on silica gel eluting with 50% EtOAc/hexane and then recrystallized from EtOAc/hexane to obtain 3.11 g.

Provenance & Evidence