反应详情

温度

92 °C

A mixture of 2-propoxy-3,5-diisopropyl-phenylboronic acid (Intermediate 4, 3.28 g, 12.4 mmol), 3-iodo-pent-2-en-1-ol (3.95 g, 18.6 mmol), Pd(PPh3)4 (720 mg, 0.62 mmol), and Na2CO3 (2M, 31 mL, 62 mmol) in toluene (40 mL) and EtOH (30 mL) was heated to 92° C. for overnight. The reaction was cooled to room temperature and extracted with EtOAc (×3). The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The additional 1.10 g of Intermediate 4 as described above was subjected to the same reaction conditions to also give crude product. The combined crude products were purified by flash column chromatography on silica gel (10% EtOAc-hexanes) to yield the title compound as a light brown oil (9.2 g, 56% over 2 steps).

1. temperatureThe reaction was cooled to room temperature
2. extractionextracted with EtOAc (×3)
3. washThe organic layer was washed with brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated in vacuo
6. customabove was subjected to the same reaction conditions
7. customto also give crude product
8. customwere purified by flash column chromatography on silica gel (10% EtOAc-hexanes)