反应详情

温度

0 °C

To an ice-cooled and stirred suspension of lithium aluminum hydride (170 mg, 4.49 mmol, 1.5 eq.) in THF (30 mL), (±)-3-(2-benzyloxy-5-fluoro-phenyl)-3H-isobenzofuran-1-one (1.0 g, 2.99 mmol, 1.0 eq.) in THF (20 mL) was added dropwise. The mixture was stirred at 0° C. for 30 min and further at r.t. for 1 hour. The mixture was again cooled to 0° C. and carefully hydrolyzed by the dropwise addition of iPrOH (15 mL) and 2M aq. NaOH (6 mL). The resulting suspension was filtered through celite and the filter cake was rinsed with THF. The fitrate was concentrated in vacuo. The residue was diluted with 2M aq. HCl soln. (150 mL) and DCM (150 mL). The layers were separated. The aq. phase was extracted with DCM (2×50 mL). The comb. org. phases were washed with water (1×150 mL), sat. aq. NaCl soln. (1×50 mL), dried over MgSO4, and concentrated in vacuo to give (±)-(2-benzyloxy-5-fluoro-phenyl)-(2-hydroxymethyl-phenyl)-methanol as a colorless oil.

1. additionwas added dropwise
2. stirringThe mixture was stirred at 0° C. for 30 min and further at r.t. for 1 hour
3. filtrationThe resulting suspension was filtered through celite
4. washthe filter cake was rinsed with THF
5. concentrationThe fitrate was concentrated in vacuo
6. additionThe residue was diluted with 2M aq. HCl soln
7. customThe layers were separated
8. extractionThe aq. phase was extracted with DCM (2×50 mL)
9. washphases were washed with water (1×150 mL), sat. aq. NaCl soln
10. dry with material(1×50 mL), dried over MgSO4
11. concentrationconcentrated in vacuo