Lithium Hydroxide → HCID 59253155, compound

HRID 386921Notes

Reaction equation

HRID 386921 reaction equation
C([O:3][C:4](=[O:17])[C:5]([CH3:16])([S:7]([CH2:10][CH2:11][C:12]([F:15])([F:14])[F:13])(=[O:9])=[O:8])[CH3:6])C.[Li+].[OH-]>C1COCC1.O>[CH3:16][C:5]([S:7]([CH2:10][CH2:11][C:12]([F:14])([F:15])[F:13])(=[O:9])=[O:8])([CH3:6])[C:4]([OH:17])=[O:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59253216HCID 59253216, compound

Product 1

HCID 59253155HCID 59253155, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

2-Methyl-2-(3,3,3-trifluoro-propane-1-sulfonyl)-propionic acid ethyl ester (1.3 g, 4.63 mmol) is dissolved in THF/water (14 mL, 4:1 ratio) and LiOH (0.2 g, 9.27 mmol, 2 eq.) is added. The mixture is stirred for 18 h at room temperature, then concentrated under reduced pressure to remove the organic solvent. The aqueous residue is further diluted with water, washed with DCM and then acidified to pH ˜2 and extracted with DCM. The combined acidic organic extracts are concentrated to afford 0.97 g of title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.72 (3H, s), 2.64-2.81 (2H, m), 3.46-3.6 (2H, m)

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the organic solvent
  3. additionThe aqueous residue is further diluted with water
  4. washwashed with DCM
  5. extractionextracted with DCM
  6. concentrationThe combined acidic organic extracts are concentrated

Sources & evidence

ORD record
ord-2db5162e83db47b09f4ee03d11c390f0
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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