Triethylamine → HCID 44241828, compound

HRID 2039424Notes

Reaction equation

HRID 2039424 reaction equation
[OH:1][CH:2]([CH3:9])[C:3]([O:5][CH2:6][CH:7]=[CH2:8])=[O:4].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C1(C)C=CC=CC=1>[CH3:17][S:18]([O:1][CH:2]([CH3:9])[C:3]([O:5][CH2:6][CH:7]=[CH2:8])=[O:4])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 953162-Propen-1-yl 2-hydroxypropanoate

Product 1

HCID 44241828HCID 44241828, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

32.00 g (246 mmol) of 2-propenyl 2-hydroxypropionate and 31.3 g (310 mmol) of triethylamine were dissolved in 150 g of toluene (solvent), and 35.6 g (310 mmol) of methanesulfonyl chloride was dropwise added thereto at 10° C., taking 20 minutes. These were reacted at room temperature for 1 hour, the reaction liquid was washed twice with water, then the organic layer was separated and concentrated. The concentrate was purified through silica gel column chromatography, and from the fraction taken with hexane/ethyl acetate=5/1, 27 g (yield 53%) of 2-propenyl 2-(methanesulfonyloxy)propionate was obtained.

Workup

  1. customThese were reacted at room temperature for 1 hour
  2. customthe reaction liquid
  3. washwas washed twice with water
  4. customthe organic layer was separated
  5. concentrationconcentrated
  6. customThe concentrate was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-7bae8482bd8d460c93e308fdf53d2970
Source dataset
uspto-grants-2013_11
Patent number
US08580429B2

Reaction notes

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