Potassium Iodide → (2RS,3RS)-2-(3,4-dichlorobenzyl)-3-(tert-butyldimethylsilyloxy)-1-(2-naphthoxy)butane

HRID 52868Notes

Reaction equation

HRID 52868 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][CH:6]([CH:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH3:10])[CH2:7][OH:8].CS(Cl)(=O)=O.C(N([CH2:33][CH3:34])CC)C.[I-].[K+].C(O[CH2:41][CH3:42])(=O)C>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][CH:6]([CH:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:16])[CH3:17])([CH3:14])[CH3:13])[CH3:10])[CH2:7][O:8][C:34]1[CH:33]=[CH:42][C:41]2[C:3](=[CH:2][CH:21]=[CH:20][CH:19]=2)[CH:4]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 19073649(2RS,3RS)-2-(3,4-dichlorobenzyl)-3-(tert-butyldimethylsilyloxy)butanol

Product 1

HCID 19073627(2RS,3RS)-2-(3,4-dichlorobenzyl)-3-(tert-butyldimethylsilyloxy)-1-(2-naphthoxy)butaneYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

200 mg of the alcohol compound thus obtained was dissolved in 5 ml of ethyl acetate, and 55 μl of methanesulfonyl chloride and 120 μl of triethylamine were added thereto with stirring under cooling with ice, and the mixture was stirred at the same temperature for 30 minutes. Formed precipitate was separated by filtration, and the filtrate was evaporated to dryness under reduced pressure. Then, the residue was dissolved in 5 ml of dimethylformamide. Separately, 87 mg of 2-naphthol was dissolved in 5 ml of dimethylformamide, and 24 mg of 60% oily sodium hydride was added. The mixture was stirred at room temperature for 30 minutes. To this solution, the dimethylformamide solution of the mesylated compound obtained above, was added under stirring. Further, 91 mg of potassium iodide was added thereto. Then, the mixture was stirred at room temperature for 3 days. The reaction solution was poured into water and extracted by an addition of ethyl ether. Then, the ether extract solution was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 77 mg (yield: 29%) of (2RS, 3RS)-2-(3,4-dichlorobenzyl)-3-(tert-butyldimethylsilyloxy)-1-(2-naphthoxy)butane.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred at the same temperature for 30 minutes
  3. customFormed precipitate
  4. customwas separated by filtration
  5. customthe filtrate was evaporated to dryness under reduced pressure
  6. dissolutionThen, the residue was dissolved in 5 ml of dimethylformamide
  7. dissolutionSeparately, 87 mg of 2-naphthol was dissolved in 5 ml of dimethylformamide
  8. addition24 mg of 60% oily sodium hydride was added
  9. stirringThe mixture was stirred at room temperature for 30 minutes
  10. customTo this solution, the dimethylformamide solution of the mesylated compound obtained above,
  11. additionwas added
  12. stirringunder stirring
  13. stirringThen, the mixture was stirred at room temperature for 3 days
  14. extractionextracted by an addition of ethyl ether
  15. extractionThen, the ether extract solution
  16. washwas washed with a saturated sodium chloride aqueous solution
  17. dry with materialdried over anhydrous magnesium sulfate
  18. customThe drying agent was separated by filtration
  19. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2a7c40b9cfdd40e895cbf4bd7cb84ca6
Source dataset
uspto-grants-1997_04
Patent number
US05616803

Reaction notes

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