Tetrahydrofuran → HCID 53656365, compound

Participants

Reaction Conditions

Reaction Steps

To 13.6 parts of the above ether in 100 parts by volume of tetrahydrofuran at -70° C is added 37 parts by volume of 2.4 molar butyl lithium in hexane. This mixture is stirred for 20 minutes at -70° C and the solution is allowed to stand for 45 minutes and then 17.8 parts of zinc iodide in 350 parts by volume of tetrahydrofuran is added while maintaining the temperature at -70° C. The resulting yellow solution is stirred for 1 hour and 8 parts of 2-hexanone in 50 parts by volume of tetrahydrofuran is added while retaining the temperature at -70° C. The reaction mixture is allowed to warm to -30° C, water is carefully added, and the reaction mixture is allowed to come to room temperature. The reaction mixture is extracted with ether, washed with water and saturated sodium chloride, and dried over anhydrous sodium sulfate. The solvent is stripped and the residual oil is distilled at 107°-110° C/0.5 mm to provide 1-trimethylsilyl-3-tetrahydropyranyloxy-4-methyl-1-octyne.

Provenance & Evidence