Lithium Hydroxide → HCID 21051842, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(4-methylsulfanyl-phenyl)-3-(tetrahydro-furan-2(R)-yl)-propionic acid methyl ester (0.693 g, 2.47 mmol) in methanol (10 mL) was treated with a 0.8M aqueous lithium hydroxide solution (4.01 mL, 4.94 mmol). The reaction mixture was stirred at 25° C. for 16 h and then was concentrated in vacuo to remove methanol. The remaining aqueous layer was acidified to pH=2 with a 10% aqueous hydrochloric acid solution and then was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×10 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford pure 2-(4-methylsulfanyl-phenyl)-3-(tetrahydro-furan-2(R)-yl)-propionic acid (0.653 g, 99%) as a light yellow oil that crystallized upon standing: mp 105-107° C.; [α]23589=−14.93° (c=0.75, chloroform); EI-HRMS m/e calcd for C14H18O3S (M+) 266.0976. found 266.0976.

Provenance & Evidence