Dimethyl Sulfoxide → HCID 21521694, compound

HRID 918277Notes

Reaction equation

HRID 918277 reaction equation
[Br:1][CH:2]=[C:3](Br)[CH:4]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].N12CCCC1=NCCC2.CS(C)=O>O>[Br:1]/[CH:2]=[CH:3]/[CH:4]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 53697152HCID 53697152, compound

Product 1

HCID 21521694HCID 21521694, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  1. temperatureis warmed at 80° for 1 hour
  2. temperaturecooled
  3. extractionextracted with ether
  4. extractionThe ethereal extract
  5. washis washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe material which remains is chromatographed on silica gel

Sources & evidence

ORD record
ord-ba2d49f59fbf4e5393e535ce71543b89
Source dataset
uspto-grants-1976_07
Patent number
US03970683

Reaction notes

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