反应详情

step a—To a solution of 4-tert-butyl-3-methoxybenzoic acid (3.00 g, 14.40 mmol, CASRN 79822-46-1) in THF (60 mL) cooled to 5° C. was added dropwise a solution of BH3-Me2S (2.0M in THF, 16.60 mL, 33.10 mmol). The reaction was allowed to stir for 24 h at RT then cooled to −50° C. and quenched by dropwise addition of MeOH (20 mL). The reaction mixture was warmed to RT and concentrated in vacuo. The residue was taken up in MeOH (3×20 mL) and concentrated in vacuo. The final residue partitioned between EtOAc and sat'd. aq. NaHCO3. The organic layer was washed with water, brine, dried (MgSO4), filtered and concentrated to afford 2.64 g (95%) of (4-tert-Butyl-3-methoxy-phenyl)-methanol (345) as a colorless oil.

1. temperaturethen cooled to −50° C.
2. customquenched by dropwise addition of MeOH (20 mL)
3. temperatureThe reaction mixture was warmed to RT
4. concentrationconcentrated in vacuo
5. concentrationconcentrated in vacuo
6. customThe final residue partitioned between EtOAc
7. washThe organic layer was washed with water, brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated