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

HRID 1381291Notes

Reaction equation

HRID 1381291 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-enantiometer 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-3d56628f55a64b718a2c08bb35e90444
Source dataset
uspto-grants-1986_04
Patent number
US04585870

Reaction notes

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