3,4-dihydro-2H-pyran → HCID 69588744, compound

Participants

Reaction Steps

A solution of Example 11A (1.62 g, 5.8 mmol), 3,4-dihydro-2H-pyran (0.64 mL, 70 mmol), and pyridinium p-toluenesulfonate (0.15 mL, 0.60 mmol) in dichloromethane (30 mL) was heated to 35° C. for 16 hours and concentrated. The concentrate was diluted with aqueous sodium hydroxide (0.25M, 15 mL) and extracted twice with ethyl acetate. The aqueous layer was adjusted to pH 3 with aqueous H3PO4 (1.0M) and extracted three times with ethyl acetate. These three extracts were combined, washed sequentially with water (20 mL) and brine (20 mL), dried (MgSO4), filtered, and concentrated to provide the desired product (0.61 g). MS (APCI(+)) m/e 364 (M+H)+.

Provenance & Evidence