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温度

0 °C

A cooled (0° C.) mixture of 4-(1-hydroxy-3-butenyl)benzonitrile (4.93 g, 28.5 mmol) and 4-(tetrahydro-2H-pyran-2-yloxy)phenol (8.3 g, 42.7 mmol) in dry THF (200 mL) was treated with tributylphosphine (8.85 mL, 42.7 mmol), followed by 1,1′-(azodicarbonyl)dipiperidine (10.77 g, 42.7 mmol). After addition was complete, the reaction mixture was stirred at 0° C. for 10 min, before being stirred at rt overnight. The precipitate of tributylphosphine oxide was removed by filtration and the filtrate was concentrated in vacuo to give 24.6 g of crude product. This was purified by chromatography on silica gel, eluting with IPA:EtOAc:heptane (5:5:90), to give 4.6 g (47%) of the subtitle compound.

1. temperatureA cooled
2. additionAfter addition
3. stirringbefore being stirred at rt overnight
4. customThe precipitate of tributylphosphine oxide was removed by filtration
5. concentrationthe filtrate was concentrated in vacuo
6. customto give 24.6 g of crude product
7. customThis was purified by chromatography on silica gel
8. washeluting with IPA:EtOAc:heptane (5:5:90)