Hydrochloric Acid → HCID 57602817, compound

Participants

Reaction Steps

Into a cooled (−78° C.) solution of 1.00 g (6.32 mmol) of (tetrahydropyran-4-yl)acetic acid methyl ester in tetrahydrofuran (20 mL) was dropped, under an atmosphere of argon, a solution of 4.5 mL (9.00 mmol) of 2 mol/L lithium diisopropylamide in hexane-heptane-ethylbenzene (available from Aldrich) and subsequently 0.47 mL (7.55 mmol) of methyl iodide, and then stirred for 30 minutes at −78° C., followed by stirring for 48 hours at room temperature. After 1N hydrochloric acid was added to the reaction mixture, it was concentrated under a reduced pressure and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was removed. The obtained residue was purified by column chromatography (silica gel 30 g, developing solvent: hexane:ethyl acetate=4: 1) to obtain 927 mg (85.1%) of 2-(tetrahydropyran-4-yl)propionic acid methyl ester (IX-166). Its physical property is shown below.

Provenance & Evidence