Cyclohexanecarboxaldehyde → HCID 54379492, compound

Participants

Reaction Steps

To a solution of N,N-diisopropyl-N-ethylamine (4.49 g) in tetrahydrofuran (50 ml) was added with stirring 1.6M n-butyl lithium in n-hexane solution (27.6 ml) below 0° C. under a nitrogen atmosphere. After the mixture was stirred in an ice-bath for 30 minutes, a solution of ethyl 3,4-methylenedioxyphenylacetate (3.85 g) in tetrahydrofuran (40 ml) was added at −78° C. The mixture was stirred for 30 minutes and cyclohexanecarbaldehyde (2.49 g) was added. After being stirred for 15 minutes at the same temperature, the mixture was quenched by saturated aqueous ammonium acetate. The mixture was extracted with diethyl ether (100 ml), and the solution was washed with 1M hydrochloric acid and brine successively, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=6:1) to give ethyl (2RS,3RS)-2-(3,4-methylenedioxyphenyl)-3-cyclohexyl-3-hydroxypropionate (4.45 g) as an oil.

Provenance & Evidence