Malonic Acid → 2-Propen-1-ol, 3-(3-pyridinyl)-

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Reaction Conditions

Reaction Steps

Triethylamine (1.4 ml) and ethyl chloroformate (0.94 ml) were added in succession to a stirred suspension of 3-(3-pyridyl)propenoic acid [1.49 g; prepared from pyridine-3-carbaldehyde and malonic acid using the general method described in Organic Synthesis, Coll, Vol. 4, 1963, 730] in tetrahydrofuran (40 ml) which had been cooled to -15° C. The mixture was stirred at this temperature for 30 minutes and then filtered. The filtrate was added over 15 minutes to a stirred solution of sodium borohydride (0.94 g) in water (8 ml) which had been cooled in an ice-bath. The mixture was stirred at ambient temperature for 3 hours then partitioned between diethyl ether and a dilute aqueous sodium hydroxide solution. The aqueous layer was extracted with diethyl ether and ethyl acetate. The combined organic extracts were washed with a saturated aqueous sodium chloride solution, dried (Na2SO4) and evaporated. The residue was purified by column chromatography eluting with toluene/ethyl acetate (1/1 v/v) to give 3-(3-pyridyl)prop-2-en-1-ol as an oil (0.84 g).

Provenance & Evidence