2-Butene-1,4-diol → 4-(4-Fluoro-3-methylbenzyloxy)but-2-en-1-ol

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Reaction Steps

To a suspension of NaH (1.0 g, 60% oil dispersion) in 80 mL THF was slowly added but-2-ene-1,4-diol (2.0 g, 22 mmol) as a solution in 5 mL THF at room temperature. To this mixture was added dropwise 4-bromomethyl-1-fluoro-2-methyl-benzene (5.0 g, 24 mmol) and the resulting stirred for 8 h at room temperature. The reaction was quenched by the slow addition of 50 mL of saturated NH4Cl and the mixture extracted with ethyl acetate (3×80 mL). The combined organic layers were washed with brine (2×60 mL) and dried over sodium sulfate. The solvent was removed under reduced pressure and the product isolated by Flash column chromatography eluting with 0% to 50% ethyl acetate/hexane to give 2.3 g of the title compound as a light yellow oil.

Provenance & Evidence