Lithium cyanide → HCID 19982141, compound

Participants

Reaction Steps

The starting material is prepared as follows: 6-Fluoro-3,4-dihydro-2H-1-benzothiopyran-3-ylacetic acid: A mixture of 3.8 g 6-fluoro-3-iodomethyl-3,4-dihydro-2H-1-benzothiopyran and 30 ml 0.5 M lithium cyanide in dimethylformamide is stirred at room temperature for 24 hours after which it is poured onto water. The product is extracted with ether. After drying over magnesium sulfate the solvent is removed in vacuo. This residue is refluxed in a mixture of 20 ml acetic acid and 20 ml 12 N HCl for 6 hours. The solvent is removed in vacuo, the residue is dissolved in 1 N NaOH and washed with ether. The aqueous phase is acidified with 3 N HCl and the product is extracted with ether. After drying over magnesium sulfate, the solvent is removed in vacuo. The residue is triturated with ether/hexane and affords the title compound, m.p. 125°-135° C.

Provenance & Evidence