Hydrochloric Acid → 5-(1,1-Difluoroethyl)-2-(trifluoromethoxy)benzaldehyde

Temperature

0 °C

To a stirred solution of Compound 24 (1.31 g, 5.22 mmol) in dry CH2Cl2(20 ml) was added a solution of diisobutylaluminum hydride(DIBAL) (6.20 ml, 6.26 mmol, 1.01M in toluene solution) with ice-cooling. The reaction mixture was stirred at 0° C. for 3 h. To the mixture was added H2O(6 ml), followed by 6M HCl aq. (20 ml) and stirred at room temperature for 1.5 h. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined solution was washed with sat. NaHCO3 aq. and brine, dried(MgSO4) and concentrated in vacuo to give crude product. The crude product was purified by column chromatography on silica gel with hexane-ethyl acetate (50:1-30:1) to give Compound 25 (1.17 g, 88%) as a yellow oil.

1. temperaturecooling
2. stirringstirred at room temperature for 1.5 h
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with CH2Cl2
5. washThe combined solution was washed with sat. NaHCO3 aq. and brine, dried(MgSO4)
6. concentrationconcentrated in vacuo
7. customto give crude product
8. customThe crude product was purified by column chromatography on silica gel with hexane-ethyl acetate (50:1-30:1)

ORD record

ord-e29c891a480e4fba8bc68dfae4669c79

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06506775B1