4-Toluenesulfonyl chloride → HCID 12553275, compound

HRID 2061022Notes

Reaction equation

HRID 2061022 reaction equation
[H-].[Na+].[C:3]([O:7][CH3:8])(=[O:6])[CH2:4][CH3:5].C([O:11][CH3:12])=O.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>CN(C=O)C>[CH3:5]/[C:4](=[CH:12]\[O:11][S:19]([C:16]1[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=1)(=[O:21])=[O:20])/[C:3]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 7865Methyl formateHCID 11124Methyl propionateHCID 24758Sodium hydride

Product 1

HCID 12553275HCID 12553275, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 10.6 g (250 mmol) of sodium hydride (60% in oil) in 150 ml of DMF was added dropwise a mixture of 20 g (226 mmol) of methyl propionate and 20.4 g (340 mmol) of methyl formate under ice cooling and stirred at room temperature overnight. To the reaction mixture was added portionwise 34.6 g (181 mmol) of p-toluenesulfonyl chloride under ice cooling and stirred at room temperature for 1 hour. After dilution with tert-butyl methyl ether, the solution was washed sequentially with water and saturated NaCl solution, dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1 to obtain 11.0 g of (E)-methyl 2-methyl-3-(p-toluenesulfonyloxy)-2-propenoate.

Workup

  1. additionwas added dropwise
  2. stirringstirred at room temperature for 1 hour
  3. washAfter dilution with tert-butyl methyl ether, the solution was washed sequentially with water and saturated NaCl solution
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1

Sources & evidence

ORD record
ord-55330aee6d984730a5c9dcdf0f4e18f0
Source dataset
uspto-grants-2012_10
Patent number
US08278473B2

Reaction notes

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