反应详情

0.61 ml (3.07 mmol) of diisopropyl diazene-1,2-dicarboxylate is added drop by dr op at 0° C. under argon to 0.5 g (2.05 mmol) of tert-butyl 4-(3-hydroxypropyl)piperazine-1-carboxylate, 0.3 g (2.46 mmol) of 4-hydroxybenzaldehyde and 1 g (3.07 mmol) of supported triphenylphosphine (3 mmol/g of resin) diluted in 14.5 ml of anhydrous tetrahydrofuran. The reaction mixture is stirred at room temperature for 20 hours, and then the solid is filtered and rinsed with dichloromethane. The filtrate is concentrated and diluted in sodium hydroxide solution (1 M), the product is extracted several times with ethyl acetate, and then the organic phases are combined, dried on magnesium sulfate and concentrated. The residue is purified by silica gel chromatography (eluent: 4:6 cyclohexane/ethyl acetate to 100% ethyl acetate) to yield 0.58 g of tert-butyl 4-(3-(4-formylphenoxy)propyl)piperazine-1-carboxylate in the form of a colorless oil.

1. filtrationthe solid is filtered
2. washrinsed with dichloromethane
3. concentrationThe filtrate is concentrated
4. additiondiluted in sodium hydroxide solution (1 M)
5. extractionthe product is extracted several times with ethyl acetate
6. customdried on magnesium sulfate
7. concentrationconcentrated
8. customThe residue is purified by silica gel chromatography (eluent: 4:6 cyclohexane/ethyl acetate to 100% ethyl acetate)