Benzenesulfonyl chloride → HCID 21387469, compound

Temperature

0 °C

Under an atmosphere of nitrogen, a solution of 4.2 g. of dimethyl 2-oxo-7-(2-tetrahydropyranyloxy)-heptylphosphonate (prepared as described above) in 15 ml. of tetrahydrofuran was added to a suspension of 596 mg. of sodium hydride (63% content) in 20 ml. of tetrahydrofuran at room temperature, and the mixture was stirred at the same temperature for 30 minutes. After cooling to 0° C., 14 ml. of a 1.3M solution of n-butyllithium in n-hexane were added to the solution and the mixture was stirred at 0° C. for 30 minutes. After cooling the solution to -78° C., there was added a solution of 3.23 g. of benzenesulphonyl chloride in 10 ml. of tetrahydrofuran. The mixture was stirred at -78° C. for one hour and then at room temperature for one hour. The reaction mixture was acidified to pH 3 with acetic acid and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and benzene (5:1) as eluent to give 2.97 g. of the title compound having the following physical characteristics:-

1. temperatureAfter cooling the solution to -78° C.
2. additionthere was added a solution of 3.23 g
3. stirringThe mixture was stirred at -78° C. for one hour
4. waitat room temperature for one hour
5. concentrationconcentrated under reduced pressure
6. dissolutionThe residue was dissolved in ethyl acetate
7. washwashed with water
8. dry with materialdried over sodium sulphate
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by column chromatography on silica gel using
11. additiona mixture of ethyl acetate and benzene (5:1) as eluent
12. customto give 2.97 g

ORD record

ord-6a87308bfd5c43458e8d3d49a6890eda

Source dataset

uspto-grants-1978_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04069387