Water → HCID 20521609, compound

Temperature

0 °C

Under an atmosphere of nitrogen, a solution of 4.2 g of the octyn-1-ol compound (prepared as described above) in 10 ml of diethyl ether was added dropwise to 12.8 ml of an 1.45 M solution of butyl lithium in hexane at 0° C., the mixture was stirred at 0° C. for 30 minutes. To the solution was added dropwise a solution of 1.58 ml of methanesulphonyl chloride in 7 ml of diethyl ether, then stirred at 0° C. for 3 hours. The mixture was poured into cold water, extracted with diethyl ether, the extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane (3:7) as eluent to give 4.1 g of the subtitle compound having the following physical characteristics:

1. stirringstirred at 0° C. for 3 hours
2. extractionextracted with diethyl ether
3. washthe extract was washed with a saturated aqueous solution of sodium chloride
4. dry with materialdried over magnesium sulphate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by column chromatography on silica gel using
7. additiona mixture of ethyl acetate and hexane (3:7) as eluent

ORD record

ord-49ac98c93b584a898cb874e3ff05acfc

Source dataset

uspto-grants-1981_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04256757