Nitromethane → 1-Benzyloxy-2-cyclopentyloxy-4-(2-nitrovinyl)benzene

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Reaction Steps

A mixture of 4-benzyloxy-3-cyclopentyloxybenzaldehyde (6.3 g, 21.3 mmol) in AcOH (13 mL) and CH3NO2 (5.8 mL, 106.5 mmol) was created. NH4OAc (3.3 g, 42.5 mmol) was added and the mixture was heated under reflux for 2 h. After cooling to r.t., the mixture was extracted with CH2Cl2. The organic layer separated and washed with water, sat. NaHCO3, and sat. NaCl, and dried over Na2SO4. Concentration under reduced pressure and purification by column chromatography on silica gel (CH2Cl2/hexane) gave 3.2 g of yellow solids. Yield: 44%.

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