p-Toluenesulfonic acid monohydrate → Methyl 3-(oxazol-2-yl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)acrylate

HRID 2375744Notes

Reaction equation

HRID 2375744 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][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[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>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[CH:14][CH:13]=1)=[CH:7][C:8]([O:10][CH3:11])=[O:9]

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 69142498Methyl 3-(oxazol-2-yl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)acrylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of compound 10.4 (2.1 mmol), p-toluenesulfonic acid monohydrate (0.57 mmol) in MeOH (15 mL) was stirred at room temperature for 1.5 hours. After quenching with saturated aqueous NaHCO3, MeOH was removed under reduced pressure. The residue was extracted with EtOAc, and the combined organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, and filtered through short plug of silica gel. Upon concentration, compound 10.3 was obtained. MS ESI (pos.) m/e 248.1 (M+1). 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 quenching with saturated aqueous NaHCO3, MeOH
  2. customwas removed under reduced pressure
  3. extractionThe residue was extracted with EtOAc
  4. washthe combined organic extracts were washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered through short plug of silica gel
  7. concentrationUpon concentration

Sources & evidence

ORD record
ord-915628061d9c4419904174253c946c76
Source dataset
uspto-grants-2008_12
Patent number
US07465804B2

Reaction notes

Loading…