Methanesulfonic Acid → HCID 66685140, compound

HRID 922240Notes

Reaction equation

HRID 922240 reaction equation
[CH3:1][C:2]1[C:6]([CH:7]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH2:8][C:9]([OH:11])=[O:10])=[C:5]([CH3:19])[O:4][N:3]=1.[CH3:20]S(O)(=O)=O>CO>[CH3:1][C:2]1[C:6]([CH:7]([C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=2)[CH2:8][C:9]([O:11][CH3:20])=[O:10])=[C:5]([CH3:19])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 66685281HCID 66685281, compound

Product 1

HCID 66685140HCID 66685140, compoundYield 18.72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a 25 mL RB flask fitted with magnetic stirrer was charged 20 mL of methanol. To the stirred solvent was added 3-(3,5-Dimethyl-1,2-oxazol-4-yl)-3-(4-hydroxyphenyl)propanoic acid (1.0 g, 6.1 mmol), followed by methanesulfonic acid (1.16 g, 12.0 mmol). After addition, the RM was refluxed at 65° C. for 1 h. After 1 h, the solvent was evaporated, water (20 mL) was added and the organic layer was extracted with ethyl acetate (15 mL×2). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as brown liquid. (0.2 g, yield: 18.72%).

Workup

  1. customTo a 25 mL RB flask fitted with magnetic stirrer
  2. additionAfter addition
  3. customthe solvent was evaporated
  4. additionwater (20 mL) was added
  5. extractionthe organic layer was extracted with ethyl acetate (15 mL×2)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. customthe solvent was removed under reduced pressure
  8. customThe product was obtained as brown liquid

Sources & evidence

ORD record
ord-8d81721dea94478c800faf5c21079b26
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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