65626-22-4

General procedure for the synthesis of 4-methyltetrahydro-2H-pyran-4-carbaldehyde from 4-(hydroxymethyl)-4-methyltetrahydropyran: To a 100 mL three-necked round-bottomed flask was added a solution of 4-(hydroxymethyl)-4-methyltetrahydropyran (compound 188.2, 300 mg, 2.30 mmol) in dichloromethane (15 mL). Subsequently, Dess-Martin reagent (1.17 g, 2.76 mmol) was added to the reaction system. The reaction mixture was stirred at room temperature for 2 hours before the reaction was quenched with 15 mL of water. The aqueous phase was extracted with 20 mL of dichloromethane and the organic layers were combined and dried over anhydrous sodium sulfate. Finally, 200 mg (68% yield) of the target product 4-methyltetrahydro-2H-pyran-4-carbaldehyde was obtained as a yellow oil by concentration under reduced pressure.

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