4-(3,4-Dichlorophenyl)butan-1-ol → HCID 54442428, compound

To a solution of Intermediate 20A (3.5 g, 16 mmol) in DCM (100 mL) was added silica gel (2.5 g) followed by pyridinium chlorochromate (4.13 g, 19.2 mmol). After stirring for 1 h, the reaction mixture was filtered and the filtrate was diluted with water and the layers were separated. The aqueous layer was further extracted with dichloromethane twice. The combined organic layers were washed with 1N HCl twice, water twice, brine twice, dried over MgSO4, filtered and concentrated. The residue was purified by ISCO chromatography (EtOAc/Hexanes 0-70%, column 40 g) to give Intermediate 20B (2.3 g, 66%) as an oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.80-1.92 (2H, m), 2.36-2.43 (2H, m), 2.50-2.60 (2H, m), 6.94 (1H, dd, J=8.3, 2.0 Hz), 7.25-7.32 (1H, m), 7.28 (1H, d, J=8.3 Hz), 9.70 (1H, s).

1. filtrationthe reaction mixture was filtered
2. additionthe filtrate was diluted with water
3. customthe layers were separated
4. extractionThe aqueous layer was further extracted with dichloromethane twice
5. washThe combined organic layers were washed with 1N HCl twice
6. dry with materialwater twice, brine twice, dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by ISCO chromatography (EtOAc/Hexanes 0-70%, column 40 g)

ORD record

ord-b119be68cec4430caf7dc5e6cd1996a8

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952180B2