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

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

ORD record

ord-cbb52df188e14a1ca2e5d0496b750bb0

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06329396B1