反应详情

温度

0 °C

BuLi (33.3 mL, 50 mmol, 1.5 M) was added in drops to a magnetically stirred solution of phenyl acetylene (5.11 g, 50 mmol) in dry tetrahydrofuran (200 mL) at 0° C. in a nitrogen atmosphere. After all the BuLi had been added, the reaction mixture was stirred at 0° C. for 30 minutes. A solution of 2-(5-iodpentyloxy)tetrahydro-2H-pyrane (9) (14.91 g, 50 mmol) in dry tetrahydrofuran (100 mL) was added in drops at 0° C. Adding completed, the reaction mixture was allowed to reach room temperature in order then to be refluxed over night. The reaction was monitored by thin-layer chromatography (TLC). When all the base material had been converted, water (300 mL) was added and the aqueous phase was extracted with petroleum ether (boiling point 40-60° C.) (6×50 mL). The combined organic phases were washed with water (4×25 mL) and dried (MgSO4). Petroleum ether was distilled out on a rotary evaporator, yielding 11.6 g (85%). NMR indicated a pure product, and further purification was therefore not necessary.

1. additionAdding
2. customto reach room temperature in order
3. temperatureto be refluxed over night
4. extractionthe aqueous phase was extracted with petroleum ether (boiling point 40-60° C.) (6×50 mL)
5. washThe combined organic phases were washed with water (4×25 mL)
6. dry with materialdried (MgSO4)
7. distillationPetroleum ether was distilled out on a rotary evaporator
8. customyielding 11.6 g (85%)
9. customa pure product, and further purification