Tetrahydrofuran → HCID 68697151, compound

HRID 1518421Notes

Reaction equation

HRID 1518421 reaction equation
[CH2:1]1[CH2:5]O[CH2:3][CH2:2]1.[CH3:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH:17]=O)[C:11]([S:19][CH3:20])=[CH:10]2.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Ti](Cl)(Cl)Cl.[Zn].C(Cl)(Cl)Cl>[CH3:3][C:2]1[CH:8]=[C:9]2[C:14](=[CH:5][CH:1]=1)[CH:13]=[C:12]([CH:17]=[CH:17][C:12]1[C:11]([S:19][CH3:20])=[CH:10][C:9]3[C:14](=[CH:15][CH:16]=[C:7]([CH3:6])[CH:8]=3)[CH:13]=1)[C:11]([S:19][CH3:20])=[CH:10]2

Participants

7

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 10340Sodium CarbonateHCID 59235946HCID 59235946, compound

Product 1

HCID 68697151HCID 68697151, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalystHCID 6212ChloroformSolvent

Procedure

Air in a 200 ml three-neck flask equipped with a dropping funnel and a reflux tube was replaced with nitrogen, and THF (31 ml) was added into the three-neck flask. While the flask was being cooled in ice bath, TiCl4 (0.35 ml, 3.2 mmol) was dropped into the flask, and subsequently zinc powder (209 mg, 3.2 mmol) was added therein. An obtained reaction solution was refluxed for 2 hours. After that, an anhydrous THF (15 ml) solution of 6-methyl-3-methylthio-2-naphthaldehyde (230 mg, 1.1 mmol) was slowly dropped into the reaction solution, and the reaction solution was refluxed for 20 hours. The reaction solution was then cooled down to a room temperature, a saturated sodium carbonate aqueous solution and chloroform were added thereto and stirred for 19 hours, and the reaction solution was filtrated so that an insoluble solid was removed. An obtained filtrate solution was extracted with chloroform, and a resultant organic layer was dried with anhydrous magnesium sulfate. A solvent was then removed therefrom by use of a rotary evaporator. An obtained yellow solid was separated and purified by silica gel column chromatography (methylene chloride solvent, column diameter: 3 cm, column length: 20 cm) so as to obtain 1,2-bis(6-methyl-3-methylthio-2-naphthyl)ethylene (131 mg, 0.33 mmol, 62%) as a yellow solid.

Workup

  1. customAir in a 200 ml three-neck flask equipped with a dropping funnel and a reflux tube
  2. additionwas added into the three-neck flask
  3. temperatureWhile the flask was being cooled in ice bath
  4. additionwas added
  5. customAn obtained reaction solution
  6. temperaturewas refluxed for 2 hours
  7. temperaturethe reaction solution was refluxed for 20 hours
  8. filtrationthe reaction solution was filtrated so that an insoluble solid
  9. customwas removed
  10. extractionAn obtained filtrate solution was extracted with chloroform
  11. dry with materiala resultant organic layer was dried with anhydrous magnesium sulfate
  12. customA solvent was then removed
  13. customby use of a rotary evaporator
  14. customAn obtained yellow solid was separated
  15. custompurified by silica gel column chromatography (methylene chloride solvent, column diameter: 3 cm, column length: 20 cm) so as

Sources & evidence

ORD record
ord-ea284303f82d4c88903eda469d5e05bf
Source dataset
uspto-grants-2012_07
Patent number
US08232546B2

Reaction notes

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