p-Toluenesulfonic acid → 4-fluorophenyl-4-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)phenyl methanone

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Reaction Steps

In an oven-dried flask placed under a nitrogen atmosphere, the product of Step 1 (121 g) and 3,4-dihydro-2H-pyran (106 mL) were stirred in dichloromethane (1100 mL). To this was added p-toluenesulfonic acid (4.4 g). The reaction mixture was stirred at room temperature for 2 hours. It was then transferred to a separatory funnel and washed with a saturated aqueous solution of sodium bicarbonate (1 L), dried over sodium sulfate and concentrated by rotary evaporation to yield an oil. 160 grams of 4-fluorophenyl-4-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)phenyl methanone was isolated. It was used in the next reaction as is without further purification.

Provenance & Evidence