Pyridine → Methyl 3-(p-tolylsulfonyloxy)-2,2-dimethylpropanoate

HRID 1593232Notes

Reaction equation

HRID 1593232 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:7][OH:8])[C:3]([O:5][CH3:6])=[O:4].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.N1C=CC=CC=1>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[CH3:1][C:2]([CH3:9])([CH2:7][O:8][S:16]([C:13]1[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=1)(=[O:18])=[O:17])[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 84152Methyl 3-hydroxypivalate

Product 1

HCID 22479327Methyl 3-(p-tolylsulfonyloxy)-2,2-dimethylpropanoateYield 108%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

A mixture of methyl 2,2-dimethyl-3-hydroxypropionate (100 g, 0.76 mol), 4-toluenesulfonyl chloride (151 g, 0.80 mol), 4-dimethylaminopyridine (4.6 g, 0.038 mol), and pyridine (200 mL) was stirred for 20 hrs and then was diluted with 200 mL toluene, stirred for 30 min and filtered. The filtrate was concentrated to 250 mL at aspirator pressure, diluted with 100 mL toluene, filtered, and concentrated. The residue was suspended in 200 mL hexanes, and the solvent was removed at aspirator pressure to yield the title compound (235 g, 100%) contaminated by a trace of toluenesulfonyl chloride.

Workup

  1. stirringstirred for 30 min
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to 250 mL at aspirator pressure
  4. additiondiluted with 100 mL toluene
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe solvent was removed at aspirator pressure

Sources & evidence

ORD record
ord-aa69c6f91ff546e69091f01a5e63b014
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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