p-Toluenesulfonic acid → HCID 69033968, compound

A solution of 4-oxo-4-(3-trifluoromethylphenyl)butyric acid methyl ester (2.47 g, 9.50 mmol), trimethylorthoformate (4.8 mL), p-TsOH (181 mg, 0.95 mmol) and ethylene glycol (7.3 mL) was heated at 50° C. for 3 h. The mixture was diluted with EtOAc (500 mL), washed with saturated NaHCO3 (3×200 mL), water (2×200 mL), and brine (150 mL), dried over Na2SO4, filtered and evaporated to give a mixture of esters. The mixture was stirred in MeOH (25 mL) with NaOMe (400 mg) at room temperature for 6 h. The reaction was quenched with saturated NH4Cl and the methanol was removed by evaporation. The residue was dissolved in EtOAc, washed with saturated NH4Cl (2×200 mL), water (2×200 mL) and brine (200 mL), dried over Na2SO4, and evaporated to give 3-[2-(3-trifluoromethylphenyl)-[1,3]dioxolan-2-yl]propionic acid methyl ester (2.71 g, 94%) as a light yellow oil: 1H NMR (300 MHz, CDCl3) δ 7.73 (s, 1H), 7.65 (d, J=7.7 Hz, 1H), 7.56 (d, J=7.7 Hz, 1H), 7.47 (t, J=7.7 Hz, 1H), 4.10–3.99 (m, 2H), 3.80–3.70 (m, 2H), 3.65 (s, 3H), 2.44 (t, J=7.8 Hz, 2H), 2.24 (t, J=7.8 Hz, 2H); 19F NMR (282 MHz, CDCl3) δ −62.9; ESI MS m/z 305 [C14H15F3O4+H]+.

1. washwashed with saturated NaHCO3 (3×200 mL), water (2×200 mL), and brine (150 mL)
2. dry with materialdried over Na2SO4
3. filtrationfiltered
4. customevaporated
5. customto give
6. customThe reaction was quenched with saturated NH4Cl
7. customthe methanol was removed by evaporation
8. dissolutionThe residue was dissolved in EtOAc
9. washwashed with saturated NH4Cl (2×200 mL), water (2×200 mL) and brine (200 mL)
10. dry with materialdried over Na2SO4
11. customevaporated

ORD record

ord-0ca5f8b960b84de2957ecec07998edc6

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07183270B2