Hydrochloric Acid → HCID 9813596, compound

Participants

Reaction Steps

163.3 mg (0.630 mmol) of palladium(II)-dichloride-diacetonitrile were dissolved in 60.00 ml of tetrahydrafuran, and 412.9 mg (1.570 mmol) of triphenylphoshine were added. The reaction mixture turned yellow and was stirred for 10 min. at room temperature. 4.198 g (28.33 mmol) of (R)-methanesulfonic acid 1-methyl-prop-2-ynylester and 3.00 g (15.74 mmol) of 2-chloro-1-(2,4-difluorophenyl)-ethanone were added as well as 42.93 ml (47.22 mmol) of diethylzinc solution in toluene (1.1 M) within 5 min. at 25–35° C. dropwise; the mixture was intermittently cooled and subsequently stirred for 40 min. at room temperature. After pouring onto 50 ml of ice-cold water and 50 ml of aqueous 25% hydrochloric acid the mixture was extracted twice with each 50 ml of ethyl acetate. The organic phases were washed once with 50 ml of water, combined, dried over sodium sulfate and evaporated to dryness. 5.029 g of (2R,3S)-1-chloro-2-(2,4-difluoro-phenyl)-3-methyl-pent-4-yne-2-ol were obtained as a dark yellow oil (73% pure) containing 76% of the stated diastereomer, corresponding to a yield of 95.3%.

Provenance & Evidence