Aluminium lithium hydride → 2,4,6-trimethyl-N-(2,2,2-trifluoro-1-hydroxymethylethyl)benzenesulfonamide

HRID 1868418Notes

Reaction equation

HRID 1868418 reaction equation
C([O:3][C:4](=O)[CH:5]([NH:10][S:11]([C:14]1[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=1[CH3:22])(=[O:13])=[O:12])[C:6]([F:9])([F:8])[F:7])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:22][C:15]1[CH:16]=[C:17]([CH3:21])[CH:18]=[C:19]([CH3:20])[C:14]=1[S:11]([NH:10][CH:5]([CH2:4][OH:3])[C:6]([F:8])([F:9])[F:7])(=[O:12])=[O:13]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57474034HCID 57474034, compound

Product 1

HCID 574740352,4,6-trimethyl-N-(2,2,2-trifluoro-1-hydroxymethylethyl)benzenesulfonamideYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.0 g (2.8 mmol) of 3,3,3-trifluoro-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid ethyl ester in 10 mL of THF was added 255 mg (6.5 mmol) of lithium aluminum hydride. The mixture stirred for 1 hour and was then cautiously quenched with water dropwise. Magnesium sulfate was then added and the mixture was filtered through CELITE® filter aid to afford 690 mg (78%) of 2,4,6-trimethyl-N-(2,2,2-trifluoro-1-hydroxymethylethyl)benzenesulfonamide.

Workup

  1. customwas then cautiously quenched with water dropwise
  2. additionMagnesium sulfate was then added
  3. filtrationthe mixture was filtered through CELITE®
  4. filtrationfilter aid

Sources & evidence

ORD record
ord-4850181ebf9e4e5db72aa1d3d5d1f740
Source dataset
uspto-grants-2009_12
Patent number
US07635711B2

Reaction notes

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