Acetic Acid → HCID 18700104、化合物

温度

-78 °C

To a stirred solution of 4-bromo-1-(tert-butyldimethylsilyloxymethyl)-2-trifluoromethoxybenzene (5.5 g, 15 mmol) from Step 3 above in THF (100 mL) at -78° C. was added n-butyllithium (6.6 mL of a 2.5 M solution in hexanes, 16.5 mmol) dropwise over a period of 10 min. The resulting pale yellow solution was stirred at -78° C. for 30 min and trimethylborate (1.75 g, 17 mmol) was added. The resulting solution was stirred at -78° C. for 5 min and then warmed to ambient temperature for 45 min. To the mixture was added acetic acid (0.90 mL, 15 mmol) and hydrogen peroxide (0.1.7 mL of a 30% solution in water, 17 mmol) and stirring was continued for 1 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (150 mL) and water (2×50 mL). The organic layer was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 10% EtOAc:hexanes as eluant to give 4-hydroxy-1-(tert-butyldimethylsilyloxymethyl)-2-trifluoromethoxy-benzene as a colorless oil (TLC Rf =0.40 (10% EtOAc:hexanes)).

1. stirringThe resulting solution was stirred at -78° C. for 5 min
2. temperaturewarmed to ambient temperature for 45 min
3. stirringstirring
4. waitwas continued for 1 h
5. customThe solvent was removed under reduced pressure
6. customthe residue was partitioned between EtOAc (150 mL) and water (2×50 mL)
7. dry with materialThe organic layer was dried (MgSO4)
8. filtrationfiltered
9. customthe solvent was removed under reduced pressure
10. customThe residue was purified by pressurized silica gel column chromatography

ORDレコード

ord-ca1a017ccf3347798652aac533aac49e

出典データセット

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06090805