Ethylacetate heptane → 3-Fluoro-2-(3-hydroxypropyl)-6-methoxyphenol

To a 50 ml solution of 4.46 g of 6-fluoro-2-hydroxy-3-methoxybenzaldehyde in dichloromethane there was added 10 g of (triphenylphosphoranilidene)acetic acid ethyl ester while cooling on ice. After stirring at room temperature for 30 minutes, the reaction mixture was poured into a silica gel column and elution was performed with heptane-ethyl acetate=3:1. The eluate was concentrated under reduced pressure. The residue was dissolved in 100 ml of ethyl acetate, and 1 g of 10% palladium-carbon was added prior to stirring for 7 hours at room temperature under a hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in 100 ml of THF, 2 g of lithium borohydride was added while cooling on ice and the mixture was stirred overnight at room temperature. After then adding 1N hydrochloric acid to the reaction mixture while cooling on ice, extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered out and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane system) to obtain the target compound (4.78 g) as a solid.