Trifluoroacetic acid → HCID 58986846, compound

To a solution of 4-[(methyloxy)methyl]-1-({[4-(methyloxy)phenyl]methyl}oxy)-2-nitrobenzene D118 (1.57 g, 5.18 mmol) in DCM (80 mL) was added trifluoroacetic acid (3.99 mL, 51.80 mmol). After 1 hr the mixture was washed with water (3×25 mL) and then extracted with 10% aq potassium carbonate solution (3×20 mL). The combined extracts were back washed with diethyl ether (20 mL) and then the pH was adjusted to 1 with 2N HCl, the mixture was extracted with DCM (3×25 mL), the combined extracts were washed with water (25 mL) and brine (25 mL), dried(MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 5-40% EtOAc in isohexane to afford the title compound as a bright yellow oil. 0.72 g, 76%

1. washAfter 1 hr the mixture was washed with water (3×25 mL)
2. extractionextracted with 10% aq potassium carbonate solution (3×20 mL)
3. washThe combined extracts were back washed with diethyl ether (20 mL)
4. extractionthe mixture was extracted with DCM (3×25 mL)
5. washthe combined extracts were washed with water (25 mL) and brine (25 mL), dried(MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by silica gel chromatography
9. washeluting with 5-40% EtOAc in isohexane

ORD record

ord-a051f1672ffc428d961cec9807f5eb4d

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426443B2