Methanesulfonyl chloride → Methyl (2R)-2-[(methylsulfonyl)oxy]propanoate

HRID 1809501Notes

Reaction equation

HRID 1809501 reaction equation
[OH:1][C@H:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4].[CH3:8][S:9](Cl)(=[O:11])=[O:10]>C1(C)C=CC=CC=1>[CH3:8][S:9]([O:1][C@H:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 637514(+)-Methyl lactate

Product 1

HCID 57320743Methyl (2R)-2-[(methylsulfonyl)oxy]propanoateYield 99.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of (R)-methyl 2-hydroxypropanoate (1.0 g, 9.61 mmol) in toluene (15 mL) was cooled to 0° C. Methanesulfonyl chloride (0.82 mL, 10.6 mmol) was added drop wise. After 2 h, the solution was warmed to room temperature and further stirred for 45 min. The resulting heavy white precipitate was removed by vacuum filtration and the clear solution was concentrated to provide 1.75 g (99%) of (R)-methyl 2-((methylsulfonyl)oxy)propanoate as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 5.14 (q, J=7.0 Hz, 1H), 3.81 (d, J=4.5 Hz, 3H), 3.16 (d, J=4.5 Hz, 3H), 1.62 (d, J=7.0 Hz, 3H). (S)-methyl 2-((methylsulfonyl)oxy)propanoate was prepared in an analogous fashion using (S)-methyl 2-hydroxypropanoate.

Workup

  1. customThe resulting heavy white precipitate was removed by vacuum filtration
  2. concentrationthe clear solution was concentrated

Sources & evidence

ORD record
ord-9851ab9c822342dfa274754d55aa441c
Source dataset
uspto-grants-2013_01
Patent number
US08362048B2

Reaction notes

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