1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 5,6-dihydro-2H-thiopyran-3-carboxylate

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Reaction Conditions

Reaction Steps

To a solution of methyl 4-((methylsulfonyl)oxy)tetrahydro-2H-thiopyran-3-carboxylate (4.33 g, 17.0 mmol) in DCM (170 mL) was added DBU (3.89 g, 25.5 mmol). The resulting mixture was refluxed at 50° C. for 30 minutes. The mixture was cooled to ambient temperature and washed with 1N aqueous HCl. The organic extract was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by MPLC on silica gel (using a gradient elution of 0-45% EtOAc/hexanes) to afford the title compound. 1H NMR (500 MHz, CDCl3): δ 7.12-7.13 (m, 1H); 3.75 (s, 3H); 3.36 (q, J=2.2 Hz, 2H); 2.68 (t, J=5.8 Hz, 2H); 2.51-2.52 (m, 2H).

Provenance & Evidence