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Triethylamine → Methyl (S)-2-methyl-3-((methylsulfonyl)oxy)propanoate

HRID 1360160
Notes
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Reaction equation

HRID 1360160 reaction equation
[CH3:1][O:2][C:3](=[O:8])[C@@H:4]([CH3:7])[CH2:5][OH:6].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(OC(=O)CC(C)=O)C>ClCCl>[CH3:1][O:2][C:3](=[O:8])[C@@H:4]([CH3:7])[CH2:5][O:6][S:17]([CH3:16])(=[O:19])=[O:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8868Ethyl AcetoacetateHCID 31297Methanesulfonyl chlorideHCID 10192563methyl (2S)-3-hydroxy-2-methylpropanoate

Product 1

HCID 11608092Methyl (S)-2-methyl-3-((methylsulfonyl)oxy)propanoateYield 100%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

3 g (25.3 mmol) of (S)-3-hydroxy-2-methyl-propionic acid methyl ester was dissolved in dichloromethane 50 mL, then 5.3 mL (37.9 mmol) of triethylamine was dropwise added thereto. Thereafter, 2.16 mL (27.9 mmol) of methanesulfonyl chloride was added to the solution at 0° C. After 1 hour, 200 mL of ethylacetoacetate was added to the solution and then the reaction solution was washed with water and then an organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, then the residue was purified by column chromatography to give 4.97 g (25.3 mmol) of the title compound in a yield of 100%.

Workup

  1. washthe reaction solution was washed with water
  2. dry with materialan organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-71898879b64a493db5528ec7feb6f1c2
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07879848B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes