Pyridine → Ethyl 2-methylsulfonyloxypropanoate

HRID 1719367Notes

Reaction equation

HRID 1719367 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C@H:2]([CH3:4])[OH:3].N1C=CC=CC=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>O>[CH3:15][S:16]([O:3][CH:2]([CH3:4])[C:1]([O:6][CH2:7][CH3:8])=[O:5])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 92831(L)-ethyl lactate

Product 1

HCID 3509469Ethyl 2-methylsulfonyloxypropanoateYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

24.11 G (0.2041 mol) of ethyl L-(+)-lactate and 50 ml of anydrous pyridine were stirred in an ice bath. 17.0 Ml (25.2 g, 0.220 mol) of methanesulfonyl chloride was added dropwise over a period of 20 minutes, and the mixture was stirred for 1 hour at the same temperature and for 1 hour at room temperature. 200 Ml of water was added, and extraction was performed with methylene chloride (50 ml, 3 times). The extract was washed with water (50 ml), then dried with anhydrous magnesium sulfate, and vacuum concentrated. The red-colored oily residue was vacuum distilled, and 32.20 g of ethyl (-)-2-methanesulfonyloxypropionate was obtained in the form of a colorless liquid with bp 97°-102° C./2 Torr. Yield 82.0%.

Workup

  1. extractionextraction
  2. washThe extract was washed with water (50 ml)
  3. dry with materialdried with anhydrous magnesium sulfate, and vacuum
  4. concentrationconcentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-8d53d4b2e3bc497c9296dae303685299
Source dataset
uspto-grants-1985_09
Patent number
US04539420

Reaction notes

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