Hydrochloric Acid → HCID 9813596, compound

16.33 mg (0.0630 mmol) of palladium(II)-dichloride-diacetonitrile were dissolved in 6.00 ml of tetrahydrofuran. 41.29 ml (0.157 mmol) of triphenylphoshine were added. The reaction mixture turned yellow and was stirred for 10 minutes at room temperature. 419.8 mg (2.833 mmol) of (R)-methanesulfonic acid 1-methyl-prop-2-ynylester and 300.0 mg (1.574 mmol) of 2-chloro-1-(2,4-difluorophenyl)-ethanone were added, also 4.293 ml (4.722 mmol) of diethylzinc solution in toluene (1.1 M) within 5 min. at 25–35° C., the latter dropwise with intermittent cooling of the reaction mixture. Stirring was continued for 45 min. at room temperature. The reaction mixture was added to 10 ml of ice-cold water and 5 ml of 25% aqueous hydrochloric acid, extracted twice with each 25 ml of ethyl acetate, the organic phases washed once with 15 ml of water, combined, dried over sodium sulfate and evaporated to dryness. 444 mg of (2R,3S)-1-chloro-2-(2,4-difluoro-phenyl)-3-methyl-pent-4-yne-2-ol were obtained as a yellow oil with purity 78.6%, which contained 77% of the stated diastereomer. Yield 90.6%.

1. temperaturethe latter dropwise with intermittent cooling of the reaction mixture
2. stirringStirring
3. waitwas continued for 45 min. at room temperature
4. extractionextracted twice with each 25 ml of ethyl acetate
5. washthe organic phases washed once with 15 ml of water
6. dry with materialdried over sodium sulfate
7. customevaporated to dryness

ORD record

ord-05e783322b3945f9814fc9642ef679f9

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07115643B2