Methanesulfonyl chloride → HCID 10130550, compound

HRID 1611052Notes

Reaction equation

HRID 1611052 reaction equation
[C:1]([OH:9])(=[O:8])[C@H:2]([CH2:4][C:5]([OH:7])=[O:6])[OH:3].[CH3:10][S:11](Cl)(=[O:13])=[O:12]>C1COCC1>[CH3:10][S:11]([O:3][C@@H:2]([CH2:4][C:5]([OH:7])=[O:6])[C:1]([OH:9])=[O:8])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 222656L-Malic Acid

Product 1

HCID 10130550HCID 10130550, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8.04 g (0.060 mol) of (S)-malic acid and 9.2 mL (0.120 mol) of methanesulphonyl chloride in 60.0 mL of THF was refluxed for 10 hours. After cooling, the solution was vacuum evaporated to dryness to obtain 12.60 g (99%) of the title compound. H-NMR in DMSO-d6: δ 2.41 (3H, s, CH3SO3), 2.90 (2H, m, CH2), 5.47 (1H, t, CHOSO2).

Workup

  1. temperatureAfter cooling
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-4598b8c4e95e4b86aa09ce692511c1d2
Source dataset
uspto-grants-2006_01
Patent number
US06984739B2

Reaction notes

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