4-Toluenesulfonyl chloride → (R)-4-(Methylthio)-2-(p-toluenesulfonyloxy)butyl p-Toluenesulfonate

HRID 1031781Notes

Reaction equation

HRID 1031781 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][C@@H:5]([OH:8])[CH2:6][OH:7].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>N1C=CC=CC=1>[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15]([O:7][CH2:6][C@H:5]([O:8][S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH2:4][CH2:3][S:2][CH3:1])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 10920564(R)-4-(methylthio)1,2-butanediol

Product 1

HCID 14634101(R)-4-(Methylthio)-2-(p-toluenesulfonyloxy)butyl p-Toluenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(R)-4-(Methylthio)-1,2-butanediol (0.4 g, 2.9 mmol) was dissolved in 5 ml of pyridine and cooled to 0°-5° C. p-Toluenesulfonyl chloride (1.65 g, 9.0 mmol) was added and, after 5 minutes, the cooling bath removed, and the mixture stirred at room temperature for 2 hours, at which point it was diluted with 15 ml of H2O and extracted with 20 ml of ethyl acetate. The organic extract was washed with saturated NaCl, dried (MgSO4) and stripped to yield 0.5 g of present, crude title product as an oil, all of which was used in the next step without further refinement; tlc Rf 0.53 (3:1 hexane:ethyl acetate), 0.25 (5:1 hexane:ethyl acetate).

Workup

  1. additionwas added and, after 5 minutes
  2. customthe cooling bath removed
  3. additionwas diluted with 15 ml of H2O
  4. extractionextracted with 20 ml of ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with saturated NaCl
  7. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-0fc8471770dc4d5ba87f076533fe9750
Source dataset
uspto-grants-1990_09
Patent number
US04954647

Reaction notes

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