p-Toluenesulfonic acid monohydrate → Methyl 3-(4-hydroxyphenyl)-3-(1,3-oxazol-2-yl)propanoate

HRID 2246645Notes

Reaction equation

HRID 2246645 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([C:12]1[CH:17]=[CH:16][C:15]([O:18]C2CCCCO2)=[CH:14][CH:13]=1)[CH2:7][C:8]([O:10][CH3:11])=[O:9].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([CH:6]([C:2]2[O:1][CH:5]=[CH:4][N:3]=2)[CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59855129Methyl 3-(oxazol-2-yl)-3-(4-(tetrahydro-2H-pyran-2-yloxy) phenyl)propanoate

Product 1

HCID 59855142Methyl 3-(4-hydroxyphenyl)-3-(1,3-oxazol-2-yl)propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of M11.4 (2.1 mmol), p-toluenesulfonic acid monohydrate (0.57 mmol) in MeOH (15 mL) was stirred at room temperature for 1.5 hours. After it was quenched with NaHCO3 (aqueous) solution, MeOH was removed by rotary evaporator. The residue was extracted with EtOAc, and the combined organic phase was washed with brine, dried over anhydrous sodium sulfate, and filtered through short plug of silica gel. After removing solvent, compound M11 was obtained. MS ESI (pos.) m/e 248.1 (M+H). 1H NMR (500 MHz) (DMSO-d6) δ 9.04 (s, 1H); 7.99 (s, 1H); 7.14 (s, 1H); 7.05 (m, 2H); 6.72 (m, 2H); 4.49-4.52 (m, 1H); 3.57 (s, 1H); 3.22-3.27 (m, 1H); 2.89-2.94 (m, 1H).

Workup

  1. customAfter it was quenched with NaHCO3 (aqueous) solution, MeOH
  2. customwas removed by rotary evaporator
  3. extractionThe residue was extracted with EtOAc
  4. washthe combined organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered through short plug of silica gel
  7. customAfter removing solvent
  8. customcompound M11 was obtained

Sources & evidence

ORD record
ord-62f7bd7b7b7741c0bbdfcbae4de223f1
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

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