3-Butyn-2-ol

The ketone (5.00 mmol) was dissolved in 50 mL of THF in a 50 mL round-bottom flask. The mixture was cooled to -78°C. At -78°C, magnesium acetylenyl chloride (5.5 mL, 5.5 mmol, 0.6 M toluene solution) was added dropwise to the mixture. The mixture was transferred to 0°C. The mixture was stirred for 1.5 hours. A saturated aqueous solution of NH4Cl (10 mL) was added to the mixture. The entire mixture was extracted with EtOAc (20 mL × 3). The combined organic layers were washed with brine (10 mL). The combined organic layers were dried with Na2SO4. The combined organic layers were filtered. The combined organic layers were concentrated under vacuum. The residue was purified by silica gel column chromatography using petroleum ether and ethyl acetate as eluents to give 3-butyn-2-ol.

Figure 3. Synthetic Route of Butyn-2-ol

clear colorless to light yellow liquid

3-Butyn-2-ol is an intermediate used to prepare aminoindanes with inhibitory activity toward acetylcholine esterase and monoamine oxidase useful as anti-Alzheimer's agents.

Flammable