Methanesulfonyl chloride → ethyl (2S)-2-methylsulfonyloxypropanoate

HRID 1722483Notes

Reaction equation

HRID 1722483 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C@H:2]([CH3:4])[OH:3].[CH3:9][S:10](Cl)(=[O:12])=[O:11]>C(N(CC)CC)C>[CH2:7]([O:6][C:1](=[O:5])[C@@H:2]([O:3][S:10]([CH3:9])(=[O:12])=[O:11])[CH3:4])[CH3:8]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 92831(L)-ethyl lactate

Product 1

HCID 6364515ethyl (2S)-2-methylsulfonyloxypropanoate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

An equal molar solution of (S)-ethyl lactate and triethylamine in dry methylene was treated with an equal molar amount of methane sulfonylchloride at 5°-10° C. After the addition was complete, the mixture was filtered to remove triethylamine hydrochloride. The filtrate was then washed with water, dried over MgSO4, and concentrated to give a high yield of ethyl-(S)-2[(methylsulfonyl)oxy]propionate.

Workup

  1. additionAfter the addition
  2. filtrationthe mixture was filtered
  3. customto remove triethylamine hydrochloride
  4. washThe filtrate was then washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e8d93e9e3636409594f61ba603ea88f8
Source dataset
uspto-grants-1989_08
Patent number
US04855455

Reaction notes

Loading…