Hydrochloric Acid → 2-Methyl-2-(4,4,4-trifluorobutane-1-sulfonyl)-propionic acid

HRID 628768Notes

Reaction equation

HRID 628768 reaction equation
C([O:3][C:4](=[O:18])[C:5]([CH3:17])([S:7]([CH2:10][CH2:11][CH2:12][C:13]([F:16])([F:15])[F:14])(=[O:9])=[O:8])[CH3:6])C.C[Si](C)(C)[O-].[K+].Cl>C1COCC1>[CH3:17][C:5]([S:7]([CH2:10][CH2:11][CH2:12][C:13]([F:15])([F:16])[F:14])(=[O:9])=[O:8])([CH3:6])[C:4]([OH:18])=[O:3]

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 592531612-Methyl-2-(4,4,4-trifluorobutane-1-sulfonyl)-propionic acidYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 170 g (585.6 mmol) 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 (1756.8 mmol) 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 2M aqueous 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-(4,4,4-trifluoro-butane-1-sulfonyl)-propionic acid as yellow solids. Yield: 93%; ES-MS: m/z 261 [M−H]. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.71 (6 H, s), 2.18-2.28 (2 H, m), 2.30-2.42 (2 H, m), 3.38 (2 H, t, J=7.48 Hz), 6.96 (1 H, br. s.).

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-a4774a912eaf418d8a6692df72c17aca
Source dataset
uspto-grants-2016_04
Patent number
US09315454B2

Reaction notes

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