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0 °C

0.5 g (2.1 mmole) 4-[2-(4-hydroxyphenyl)ethoxy]benzaldehyde was dissolved in tetrahydrofuran, cooled to 0° C. and 0.092 g (2.1 mmole) sodium hydride in tetrahydrofuiran was added. The reaction mixture was stirred until gas development ceased, then 0.4 g (4 mmole) tert-butyl isocyanate in tetrahydrofuran was added and the temperature was allowed to rise to room temperature. The reaction was followed by TLC. More 0.4 g (4 mmole) tert-butyl isocyanate was added. After 3 days the reaction was quenched with ice and sodium hydroxide (aq), extracted with dichloromethane, dried and evaporated. Purification by chromatography on silica gel using ethyl acetate:petroleum ether (1:2) as eluent gave 0.6 g (yield 84%) of 4-[2-(4-formylphenoxy)ethyl]phenyl N-(tert-butyl)carbamate.

1. customto rise to room temperature
2. customAfter 3 days the reaction was quenched with ice and sodium hydroxide (aq)
3. extractionextracted with dichloromethane
4. customdried
5. customevaporated
6. customPurification by chromatography on silica gel