反应详情

To MeOH (140 mL) solution containing KOH (4.73 g, 84.3 mmol) at 22° C. was added 2-bromo-4-fluorophenol (16.09 g, 84.2 mmol) and 2-pentyne-1,5-diol ditosylate (11.47 g, 28.1 mmol). After stirring 20 h acetic acid (3.5 mL) was added and the reaction stirred 1 h. The reaction was concentrated in vacuo and the residue extracted with CH2Cl2 (75 mL) and saturated K2CO3 (75 mL). The organic phase was separated and washed with saturated K2CO3. The aqueous phase was washed with CH2Cl2 (2×30 mL). The combined CH2 Cl2 layers were dried with dried with MgSO4, filtered, concentrated in vacuo. Silica gel chromatography (9:1 Hexane:EtOAc) yielded the title compound as a viscous oil (8.39 g, 70%).

1. additionwas added
2. concentrationThe reaction was concentrated in vacuo
3. extractionthe residue extracted with CH2Cl2 (75 mL) and saturated K2CO3 (75 mL)
4. customThe organic phase was separated
5. washwashed with saturated K2CO3
6. washThe aqueous phase was washed with CH2Cl2 (2×30 mL)
7. dry with materialThe combined CH2 Cl2 layers were dried
8. dry with materialwith dried with MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo