Potassium Iodide → HCID 178444529, compound

HRID 1849922Notes

Reaction equation

HRID 1849922 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH:12]=[CH:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[H-].[Na+].[I-].[K+].[CH2:21]([C@H:26]1[CH2:31][CH2:30][C@H:29]([CH2:32]Br)[CH2:28][CH2:27]1)[CH2:22][CH2:23][CH2:24][CH3:25]>C1COCC1.O>[CH2:1]([C@H:4]1[CH2:5][CH2:6][C@H:7]([CH:10]2[CH:15]=[CH:14][CH:13]([O:16][CH2:32][C@H:29]3[CH2:30][CH2:31][C@H:26]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:27][CH2:28]3)[CH2:12][CH2:11]2)[CH2:8][CH2:9]1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 178444389HCID 178444389, compoundHCID 178447903HCID 178447903, compound

Product 1

HCID 178444529HCID 178444529, compoundYield 3.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, 2.4 g of 4-(trans-4-propylcyclohexyl)-2-cyclohexene-1-ol (r-1) was dissolved into 50 mL of THF, 0.52 g of 60% sodium hydride was added under ice-cooling, and the resultant mixture was stirred at room temperature for 1 hour. Thereto, 2.3 g of potassium iodide and 3.2 g of (trans-4-pentylcyclohexyl)bromomethane (r-2) dissolved in 30 mL of THF were added, and the resultant mixture was stirred under heating reflux for 8 hours. The resultant reaction mixture was poured into water, and subjected to extraction with toluene. Combined organic layers were washed with saturated brine, and then dried over anhydrous magnesium sulfate. A solvent was evaporated under reduced pressure, and a residue was purified by silica gel column chromatography (eluate:heptane:toluene=1:1 (in a volume ratio)), and further purified by recrystallization from a mixed solvent of heptane:Solmix A-11 (registered tradename; Japan Alcohol Trading Co., Ltd.)=1:2 (in a volume ratio), and thus 0.15 g of 6-(trans-4-propylcyclohexyl)-3-(trans-4-pentylcyclohexyl)methoxy cyclohexene [compound (1-3-1-18) was obtained.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. additionwere added
  4. temperatureunder heating
  5. temperaturereflux for 8 hours
  6. customThe resultant reaction mixture
  7. extractionsubjected to extraction with toluene
  8. washCombined organic layers were washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customA solvent was evaporated under reduced pressure
  11. customa residue was purified by silica gel column chromatography (eluate:heptane
  12. customtoluene=1:1 (in a volume ratio)), and further purified by recrystallization from a mixed solvent of heptane

Sources & evidence

ORD record
ord-3ed26e9f75214a168627206fa4673557
Source dataset
uspto-grants-2015_02
Patent number
US08956552B2

Reaction notes

Loading…