Dimethyl Sulfoxide → HCID 21521694, compound

Participants

Reaction Steps

A mixture of 3.7 parts of 1,2-dibromo-3(RS)-(tetrahydropyran-2-yl)oxy-1-octene, 1.25 parts of 1,5-diazabicyclo[4.3.0]non-5-ene and 25 parts by volume of dimethyl sulfoxide is warmed at 80° for 1 hour, then cooled, diluted with water and extracted with ether. The ethereal extract is washed with water, dried over anhydrous sodium sulfate and stripped of solvent. The material which remains is chromatographed on silica gel to yield 1-bromo-3(RS)-(tetrahydropyran-2-yl)oxy-trans-1-octene, which is employed in the same manner as the iodooctene compound in Example 25 to produce the organo-copper compound, 3(RS)-(tetrahydropyran-2-yl)oxy-1-octenyl copper. That material is employed in situ as described in Example 25 to afford the products of Example 25.

Provenance & Evidence