1-Iodonaphthalene → HCID 15742917, compound

HRID 1351063Notes

Reaction equation

HRID 1351063 reaction equation
[CH:1]1([SH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O-]CC.[Na+].I[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.CC(CC(C)C)=O>C(O)C.O>[CH:1]1([S:7][C:21]2[C:22]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:18]=[CH:19][CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 70041-IodonaphthaleneHCID 7909Methyl Isobutyl KetoneHCID 15290CyclohexanethiolHCID 2723922Sodium ethoxide

Product 1

HCID 15742917HCID 15742917, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

33.5 g of cyclohexanethiol, 37.4 g of sodium ethoxide, and 70 g of 1-iodonaphthalene was dissolved in 1 l of ethanol in a reaction flask, in which the atmosphere was replaced with nitrogen. 3.2 g of tetrakis(triphenylphosphonium)palladium was added. The mixture was stirred for 11 hours at 90° C. Ethanol was condensed under reduced pressure and 1 l of methyl isobutylketone and 1 l of distilled water were added. The mixture was transferred to a separatory funnel, shaken, and allowed to stand still. The water layer was removed. 1 l of distilled water was added and the mixture was shaken again and allowed to stand still. The water layer was removed. The resulting solution was dried with anhydrous magnesium sulfate and filtered. After further drying using an evaporator, methyl isobutylketone was evaporated from the dried solution. The residual liquid was dried under reduced pressure and was purified by a silica gel column using n-hexane as a developing solvent. The n-hexane was evaporated under reduced pressure to obtain 46 g of 1-cyclohexylthionaphthalene.

Workup

  1. additionwere added
  2. customThe mixture was transferred to a separatory funnel
  3. stirringshaken
  4. customThe water layer was removed
  5. addition1 l of distilled water was added
  6. stirringthe mixture was shaken again
  7. customThe water layer was removed
  8. dry with materialThe resulting solution was dried with anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customAfter further drying
  11. customan evaporator, methyl isobutylketone
  12. customwas evaporated from the dried solution
  13. customThe residual liquid was dried under reduced pressure
  14. customwas purified by a silica gel column
  15. customThe n-hexane was evaporated under reduced pressure

Sources & evidence

ORD record
ord-071172cb4c964aebb0ec92ee2e1f0ef2
Source dataset
uspto-grants-2007_05
Patent number
US07217492B2

Reaction notes

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