反应详情

温度

-78 °C

To 500 ml THF cooled to -78° C. is added butyl lithium (2 eq.) followed by 4-bromobenzyl alcohol (27.2 g; 145 mmol) slowly over 45 minutes in a solution of THF (100 ml) keeping the temperature below -72° C. After 10 minutes following the final addition of the alcohol is added 2-chlorobenzoxazole (23.3 g; 145 mmol) in 25 ml THF slowly over 45 minutes. The temperature is maintained at -78° C. for 1 hour and then warmed to -40° C. for 15 minutes. The reaction is then quenched with 15 ml of acetic acid and allowed to warm to room temperature, diluted with 800 ml ether, washed 3× with H2O and brine, dried (MgSO4) and concentrated in vacuo to obtain a brown oily solid which is washed with 400 ml petroleum ether and filtered to obtain 4-(benzoxazol-2-yl)benzyl alcohol as a tan solid which is used directly in Step B.

1. customthe temperature below -72° C
2. temperaturewarmed to -40° C. for 15 minutes
3. customThe reaction is then quenched with 15 ml of acetic acid
4. temperatureto warm to room temperature
5. additiondiluted with 800 ml ether
6. washwashed 3× with H2O and brine
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo
9. customto obtain a brown oily solid which
10. washis washed with 400 ml petroleum ether
11. filtrationfiltered