Pyridine → (4S)-1-methylsulfonyloxy-4-(2-tetrahydropyranyloxy)-nonane

Participants

Reaction Steps

A mixture of (4S)-4-(2-tetrahydropyranyloxy)-1-nonanol (29.2 g., 0.12 mole) and pyridine (20 ml.) is cooled to 5° by means of an ice bath. Methanesulfonyl chloride (17.2 g., 0.15 mole) is added dropwise during 20 minutes and the mixture is stirred 4 hours with ice bath cooling. The mixture is then taken up in ether, washed with 4 portions of water and with brine and dried over sodium sulfate. The ether is distilled on the rotary evaporator to leave as a residual oil crude (4S)-1-methylsulfonyloxy-4-(2-tetrahydropyranyloxy)-nonane.

Provenance & Evidence