Hydrochloric Acid → 2-Methyl-2-(3-methyl-butane-1-sulfonyl)-propionic acid

HRID 538639Notes

Reaction equation

HRID 538639 reaction equation
C([O:3][C:4](=[O:18])[C:5]([CH3:17])([S:7]([CH2:10][CH2:11][CH2:12][C:13](F)(F)F)(=[O:9])=[O:8])[CH3:6])C.[CH3:19][Si](C)(C)[O-].[K+].Cl>C1COCC1>[CH3:17][C:5]([S:7]([CH2:10][CH2:11][CH:12]([CH3:13])[CH3:19])(=[O:8])=[O:9])([CH3:6])[C:4]([OH:3])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668039Potassium trimethylsilanolateHCID 592532852-Methyl-2-(4,4,4-trifluoro-butane-1-sulfonyl)-propionic acid ethyl ester

Product 1

HCID 592532112-Methyl-2-(3-methyl-butane-1-sulfonyl)-propionic acidYield 109%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 170 g (0.59 mol) of 2-methyl-2-(4,4,4-trifluoro-butane-1-sulfonyl)-propionic acid ethyl ester in THF (3.4 L) are added 225.4 g (1.76 mol) of potassium trimethylsilanolate in portions over 0.5 h. The reaction is stirred at room temperature for 18 h. The reaction mixture is acidified with 2 M aq. HCl solution (2 L) to pH 2 and extracted with DCM (2×2 L). The combined organic extracts are dried (Na2SO4) and filtered. The filtrate is concentrated under reduced pressure to afford 143 g of 2-methyl-2-(3-methyl-butane-1-sulfonyl)-propionic acid.

Workup

  1. extractionextracted with DCM (2×2 L)
  2. dry with materialThe combined organic extracts are dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-47f497e3014247a3a35ad09bbd1c39c4
Source dataset
uspto-grants-2014_10
Patent number
US08865744B1

Reaction notes

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