Toluene → 2-(Pyrazol-1-yl)-ethyl 2-tosyloxy-propionate

HRID 462876Notes

Reaction equation

HRID 462876 reaction equation
[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([OH:4])(=[O:3])=[O:2].[C:12](Cl)(=[O:16])[CH:13]([CH3:15])O.[OH:18][CH2:19][CH2:20][N:21]1[CH:25]=[CH:24][CH:23]=[N:22]1.C(N(CC)CC)C.C1(C)C=CC=CC=1>O>[S:1]([O:4][CH:13]([CH3:15])[C:12]([O:18][CH2:19][CH2:20][N:21]1[CH:25]=[CH:24][CH:23]=[N:22]1)=[O:16])([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(=[O:3])=[O:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 2370311-(2-Hydroxyethyl)-1H-pyrazoleHCID 88643831Lactyl chloride tosylate

Product 1

HCID 133390282-(Pyrazol-1-yl)-ethyl 2-tosyloxy-propionate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.25 g (0.02 mol) of the S-enantiomer of lactyl chloride tosylate were added to a mixture of 2.24 g (0.02 mol) of 1-(2-hydroxyethyl)-pyrazole, 2 g (0.02 mol) of triethylamine and 50 ml of toluene at 20° C., while stirring. The reaction mixture was stirred at 20° C. for a further 14 hours and then worked up by adding water, extracting the mixture several times with toluene, drying the combined organic phases and concentrating them by stripping off the solvent under reduced pressure. 4.7 g (69.5% of theory) of the S-enantiomer of 2-(pyrazol-1-yl)-ethyl 2-tosyloxy-propionate were obtained in this manner.

Workup

  1. stirringThe reaction mixture was stirred at 20° C. for a further 14 hours
  2. extractionextracting the mixture several times with toluene
  3. customdrying the combined organic phases
  4. concentrationconcentrating them

Sources & evidence

ORD record
ord-312a80bd9fa6498ea0e5d25145355ed8
Source dataset
uspto-grants-1985_05
Patent number
US04518416

Reaction notes

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