Triethylamine → Methanesulfonyloxy(4-methanesulfonyloxyphenyl)-acetic acid methyl ester

HRID 2306617Notes

Reaction equation

HRID 2306617 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C:7]1[CH:19]=[CH:18][C:10]([CH:11]([OH:17])[C:12]([O:14][CH2:15]C)=[O:13])=[CH:9][CH:8]=1.C(N(CC)CC)C>CN(C=O)C.O>[CH3:15][O:14][C:12](=[O:13])[CH:11]([O:17][S:2]([CH3:1])(=[O:4])=[O:3])[C:10]1[CH:18]=[CH:19][C:7]([O:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 111357Benzeneacetic acid, alpha,4-dihydroxy-, ethyl ester

Product 1

HCID 88018735Methanesulfonyloxy(4-methanesulfonyloxyphenyl)-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methanesulfonyl chloride (0.395 ml, 5.10 mmol) is added dropwise at 0° C. to ethyl 4-hydroxymandelate (0.500 g, 2.55 mmol) and triethylamine (0.889 ml, 6.38 mmol) in DMF (5 ml) and the mixture is allowed to warm to room temperature overnight. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with brine, dried (MgSO4), and evaporated to give oily residue which is purified by flash column chromatography (30% EtOAc/Hexane) (0.75 g, 82%). MS (m/z): [M+H]+=353.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give oily residue which
  6. customis purified by flash column chromatography (30% EtOAc/Hexane) (0.75 g, 82%)

Sources & evidence

ORD record
ord-0f02e586205a4cb9b87e93177351fb27
Source dataset
uspto-grants-2004_12
Patent number
US06828317B2

Reaction notes

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