4-Toluenesulfonyl chloride → 2,2-Dimethyl-6-fluoro-3-[2-(4-toluenesulfonyloxy)ethyl]-chroman

HRID 1196057Notes

Reaction equation

HRID 1196057 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][C:13]1([CH3:27])[CH:22]([CH2:23][CH2:24][OH:25])[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([F:26])[CH:19]=2)[O:14]1>N1C=CC=CC=1>[CH3:12][C:13]1([CH3:27])[CH:22]([CH2:23][CH2:24][O:25][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([F:26])[CH:19]=2)[O:14]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 537581732,2-Dimethyl-6-fluoro-3-(2-hydroxyethyl)-chroman

Product 1

HCID 543823572,2-Dimethyl-6-fluoro-3-[2-(4-toluenesulfonyloxy)ethyl]-chroman

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4.01 g (21 mmol) of 4-toluenesulfonyl chloride are added while stirring at room temperature to a solution of 4.48 g (20 mmol) of 2,2-dimethyl-6-fluoro-3-(2-hydroxyethyl)-chroman in 30 ml of absolute pyridine, the slightly exothermic reaction being maintained at room temperature with an ice bath. The reaction mixture is then stirred at room temperature for 2 hours, then poured onto ice-water and the mixture is extracted with diethyl ether. The combined organic phases are washed while cold with 2N hydrochloric acid and then with water, dried over sodium sulfate and concentrated by evaporation in vacuo, yielding 6.5 g (85.8% of the theoretical yield) of 2,2-dimethyl-6-fluoro-3-[2-(4-toluenesulfonyloxy)ethyl]-chroman in the form of a light-yellow oil.

Workup

  1. customthe slightly exothermic reaction
  2. additionpoured onto ice-water
  3. extractionthe mixture is extracted with diethyl ether
  4. washThe combined organic phases are washed while cold with 2N hydrochloric acid
  5. dry with materialwith water, dried over sodium sulfate
  6. concentrationconcentrated by evaporation in vacuo
  7. customyielding 6.5 g (85.8% of the

Sources & evidence

ORD record
ord-3b1cbc5d09b0499798a421f4b46565c6
Source dataset
uspto-grants-1992_05
Patent number
US05112855

Reaction notes

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