4-Hydroxybenzaldehyde → HCID 16220388, compound

Participants

Reaction Steps

To a solution of 4-hydroxybenzaldehyde (500 mg, 4.09 mmol) and morpholine (356 mg, 4.09 mmol) in methanol (10 mL) was added macroporous triethylammonium methylpolystyrene borohydride (2.0 g, 6.0 mmol) and the mixture was stirred at ambient temperature for about 2 days. The mixture was filtered and concentrated under vacuum. The residue was dissolved in tetrahydrofuran (20 mL) and to this solution was added propargyl alcohol (229 mg, 4.09 mmol), diphenylphosphino-polystyrene (5.1 g, 8.18 mmol) and diethyl azodicarboxylate (1.06 g, 6.13 mmol). After stirring overnight at room temperature, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by flash chromatography on silica gel using diethyl ether/n-pentane (1:3) as eluent to provide Example 635. MS (DCI-NH3): m/z 232 (M+H)+.

Provenance & Evidence