反应详情

9-Borabicyclo[3.3.1]nonane (9-BBN) dissolved in 15 ml of tetrahydrofuran (manufactured by Aldrich Co.) was added to 300 mg (3.483 mmol) of 4-pentene-1-ol and allowed to react at 25° C. for 24 hours. Then, 4-bromopyridine hydrochloride (manufactured by Aldrich Co.) dissolved in water/dimethylformamide (DMF) at a ratio of 2:8, tetrakis(triphenylphosphine)palladium (manufactured by Aldrich Co.), and potassium carbonate (manufactured by Aldrich Co.) were added thereto in an equivalent ratio of 1:1.2:0.2 and allowed to react at 70° C. for 6 hours. Then, solvent was removed under reduced pressure, and the residual material was diluted with ethyl acetate and filtered with Celite. The material thus obtained was purified by column chromatography (column: silica (manufactured by Aldrich Co.), solvent: ethyl acetate/hexane) to obtain 203 mg of pyridinepentanol (yield rate: 48%). The reaction scheme is shown below.

1. customto react at 25° C. for 24 hours
2. additionwere added
3. customto react at 70° C. for 6 hours
4. customThen, solvent was removed under reduced pressure
5. additionthe residual material was diluted with ethyl acetate
6. filtrationfiltered with Celite
7. customThe material thus obtained
8. customwas purified by column chromatography (column: silica (manufactured by Aldrich Co.), solvent: ethyl acetate/hexane)