Toluene → HCID 86759233, compound

HRID 478998Notes

Reaction equation

HRID 478998 reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:10]=[C:11]([C@@H:15]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH2:16][OH:17])[CH:12]=[CH:13][CH:14]=1.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>C(N(CC)CC)C>[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31]([O:17][CH2:16][C@@H:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([Cl:8])[CH:10]=2)[O:18][C@H:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 73974-Toluenesulfonyl chlorideHCID 15606325HCID 15606325, compound

Product 1

HCID 86759233HCID 86759233, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into toluene (20 ml) were added (R)-2-(3-chlorophenyl)-2-(3,4,5,6-tetrahydro-[2H]-pyran-2-yloxy)ethanol obtained in 3) above (6.0 g) and triethylamine (4.7 g) and further, under ice-cooling and dropwise, p-toluenesulfonyl chloride (4.9 g), and the resulting mixture was stirred at the same temperature for 1 hour. The reaction mixture was washed with water and the organic layer was further washed with a saturated aqueous sodium chloride solution and dried with anhydrous magnesium sulfate. The desiccant was filtered off and then the solvent was distilled off to obtain a colorless oily compound mentioned above (9.1 g, 94.8%).

Workup

  1. temperaturefurther, under ice-cooling
  2. washThe reaction mixture was washed with water
  3. washthe organic layer was further washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationThe desiccant was filtered off
  6. distillationthe solvent was distilled off
  7. customto obtain a colorless oily compound

Sources & evidence

ORD record
ord-abfe105c847d45cca256199d0c66fea7
Source dataset
uspto-grants-2003_11
Patent number
US06642395B1

Reaction notes

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