Acetone → HCID 12892725, compound

To a stirred solution of 2 (1.98 mmol, 360 mg) in acetone (7.76 mL) was added 10% aqueous hydrochloric acid solution (3.02 mL), and the resulting mixture was stirred at room temperature for 2.5 hours. The reaction mixture was then diluted with brine (40 mL) and extracted with methylene chloride/ethyl ether (1:2, 3×30 mL). The organic layers were combined and washed with saturated aqueous sodium bicarbonate solution (2×30 mL) and brine (1×30 mL), then dried over magnesium sulfate, filtered, and concentrated in vacuo to give 19 (251.6 mg, 1.92 mmol, 94%) as a yellow oil that was used in the next reaction without further purification: 1H NMR (CDCl3) δ 5.89 (1H, dd, J=0.5, 17.3 Hz), 5.15 (1H, dd, J=1, 3.5 Hz), 5.12 (1H, dd, J=0.5, 10 Hz), 2.42-2.28 (4H, m), 1.97-1.91 (2H, m), 1.74-1.68 (2H, m), 1.12 (3H, s); 13C NMR (CDCl3) δ 212.4, 145.5, 112.9, 38.2, 37.1, 27.4; MS (EI) m/z 138.1 [M+], 123.1, 110.1, 105.1, 97.1, 86.0 (100%), 68.1, 63.0, 54.9; HRMS (EI) calcd for C9H14O 138.1045 found 138.1048.

1. extractionextracted with methylene chloride/ethyl ether (1:2, 3×30 mL)
2. washwashed with saturated aqueous sodium bicarbonate solution (2×30 mL) and brine (1×30 mL)
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo

ORD record

ord-26430c305a444f9e821d0fa7ff3ed3ba

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000188B2