Methyl vinyl sulfone → 4-(Methylsulfonyl)cyclohexanone

A solution containing (buta-1,3-dien-2-yloxy)(trimethyl)silane (12.5 ml, 70.7 mmol) in toluene (50 ml), was treated with (methylsulfonyl)ethene (4.1 ml, 47.1 mmol) and heated under reflux for 76 hours. After which time, the reaction mixture was cooled to room temperature and concentrated in-vacuo to give a yellow oil. The oil was dissolved in CH2Cl2 (120 ml) and filtered through Celite®. The filtrate was concentrated in-vacuo and the resulting residue was then dissolved in MeOH (8 ml) with cooling (ice/water). It was then treated with TFA (2.0 ml). The reaction mixture was stirred at 0° C. for a further 10 minutes and then at room temperature for 25 hours. The reaction mixture was concentrated in-vacuo and the residue was purified by flash column chromatography (0-10% MeOH/CH2Cl2) 100 g SNAP cartridge on the Biotage Isolera to give the title compound 1.2 g (14%) as a thick yellow oil. LC-MS 94%, 0.39 min (3.5 minute LC-MS method), m/z=177.0 (ELS visible only). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 3.24-3.32 (m, 1H) 2.94 (s, 3H) 2.62-2.70 (m, 2H) 2.50-2.56 (m, 2H) 2.38-2.45 (m, 2H) 2.07-2.18 (m, 2H).

1. temperatureheated
2. temperatureunder reflux for 76 hours
3. concentrationconcentrated in-vacuo
4. customto give a yellow oil
5. filtrationfiltered through Celite®
6. concentrationThe filtrate was concentrated in-vacuo
7. dissolutionthe resulting residue was then dissolved in MeOH (8 ml)
8. temperaturewith cooling (ice/water)
9. additionIt was then treated with TFA (2.0 ml)
10. waitat room temperature for 25 hours
11. concentrationThe reaction mixture was concentrated in-vacuo
12. customthe residue was purified by flash column chromatography (0-10% MeOH/CH2Cl2) 100 g SNAP cartridge on the Biotage Isolera

ORD record

ord-457005cf08bb4c999d05636ff6094d92

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376422B2