3,4-dihydro-2H-pyran → HCID 118021717, compound

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Reaction Steps

To the title compound of step 3 (1.0 g, 3.4 mmol) in CH2Cl2 (10 mL) was added 3,4-dihydro-2H-pyran (1.4 g, 17.0 mmol) followed by pyridinium p-toluensulfonate (64.6 mg, 0.34 mmol). After stirring at r.t. 12 h, the mixture was subjected to CH2Cl2 extractive work up & silica gel chromatography (PE: EA=1:0-5:1) to give the title compound (1.1 g, 85.6%) as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 8.11 (d, J=2.4 Hz, 1H), 7.86 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 7.00 (d, J=8.8 Hz, 1H), 4.51 (dd, J1=4.0 Hz, J2=2.4 Hz, 1H), 4.09-4.03 (m, 1H), 3.98 (s, 3H), 3.84-3.79 (m, 1H), 3.79-3.74 (m, 1H), 3.50-3.46 (m, 1H), 3.45-3.42 (m, 2H), 1.58-1.37 (m, 6H). LCMS: 401.0, 403.0 (M+Na)+.

Provenance & Evidence