Hydrochloric Acid → HCID 9813596, compound

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%.

1. additionwere added
2. temperaturethe mixture was intermittently cooled
3. stirringsubsequently stirred for 40 min. at room temperature
4. extractionwas extracted twice with each 50 ml of ethyl acetate
5. washThe organic phases were washed once with 50 ml of water
6. dry with materialdried over sodium sulfate
7. customevaporated to dryness

ORD record

ord-ada3da6577f64cae8f6392d137252407

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07115643B2