Methanesulfonic Acid → Methyl 3-(4-hydroxyphenyl)-3-(1,2-oxazol-3-yl)propanoate

HRID 922201Notes

Reaction equation

HRID 922201 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:17]=[CH:16][O:15][N:14]=2)[CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[CH3:18]S(O)(=O)=O>CO>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:17]=[CH:16][O:15][N:14]=2)[CH2:9][C:10]([O:12][CH3:18])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 592184473-(4-Hydroxyphenyl)-3-(1,2-oxazol-3-yl)propanoic acid

Product 1

HCID 66684900Methyl 3-(4-hydroxyphenyl)-3-(1,2-oxazol-3-yl)propanoateYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a 100 mL RB flask fitted with magnetic stirrer was charged 20 mL of methanol. To the stirred solvent added 3-(4-hydroxyphenyl)-3-(1,2-oxazol-3-yl) propanoic acid (1.48 g, 6.34 mmol) and cooled to 0° C., added 1 mL of methanesulfonic acid. The resulting mixture was stirred at reflux temperature for 2 h. After completion of the reaction (reaction monitored by TLC), the solvent was removed under reduced pressure and the crude mass was dissolved in ethyl acetate (25 mL). The organic layer was washed with water (50 mL), saturated brine solution (50 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as pale yellow color oil (0.69 g, Yield: 44%): MS (ESI, 120 eV): m/z=248.9 (M+H)+; 1H NMR (300 MHz, CDCl3): δ 8.20 (s, 1H), 7.01-7.04 (d, 2H), 6.66-6.69 (d, 2H), 6.00 (d, 1H), 5.56 (bro s, 1H), 4.46-4.51 (t, 1H), 3.56 (s, 3H), 3.17-3.25 (q, 1H), 2.83-2.91 (q, 1H).

Workup

  1. customTo a 100 mL RB flask fitted with magnetic stirrer
  2. temperatureat reflux temperature for 2 h
  3. customAfter completion of the reaction (reaction monitored by TLC)
  4. customthe solvent was removed under reduced pressure
  5. dissolutionthe crude mass was dissolved in ethyl acetate (25 mL)
  6. washThe organic layer was washed with water (50 mL), saturated brine solution (50 mL)
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-180cd5796ece4bb6a6de6f4f6727588b
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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