Water → 4-(3-Cyclohexyl-1-butoxyprop-2-yloxymethyl)-2-(2-methylphenyl)benzoic acid, methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-3-cyclohexyl-1-butoxy-2-propanol (example 1308D, 1.0 g) in DMF (15 mL) was added NaH (0.184 g of a 60% oil dispersion). After 15 min, the reaction was chilled to 0° C., and 4-iodomethyl-2-(2-methylphenyl)benzoic acid, methyl ester (example 1308E, 1.54 g) was added. After 45 min, the reaction was poured into water (150 mL), and extracted with EtOAc (2×75 mL). The organic extracts were washed with brine (20 mL), dried (MgSO4), filtered and concentrated. The residue was purified by silica gel chromatography eluting with 5% EtOAc/hexane to give a colorless oil (1.18 g, 62%).

Provenance & Evidence