Acetic Acid → HCID 20358652, compound

HRID 2194931Notes

Reaction equation

HRID 2194931 reaction equation
C[O:2][C:3](=[O:15])[CH:4]([C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]=[N:11][C:10]=2[CH:14]=1)[CH3:5].[Li+].[OH-].C(O)(=O)C>C1COCC1.O>[O:13]1[C:9]2[CH:8]=[CH:7][C:6]([CH:4]([CH3:5])[C:3]([OH:15])=[O:2])=[CH:14][C:10]=2[N:11]=[CH:12]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 57742184HCID 57742184, compound

Product 1

HCID 20358652HCID 20358652, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

methyl-2-(benzo[d]oxazol-5-yl)propanoate (2.07 mmol, 425 mg) was dissolved in THF (8 ml) and water (8 m). LiOH*H2O (2.21 mmol, 93 mg) was added at room temperature. The reaction mixture was stirred at room temperature for 40 h, water (25 ml) was added and the pH was set to 3 with acetic acid. The reaction mixture was extracted with dichloromethane and the combined organic phases were dried and filtered over magnesium sulphate. The solvent was removed in a vacuum and the residue was purified by column chromatography (SiO2, dichloromethane/MeOH=15:1). 1H-NMR (CD3OD) δ [ppm]: 8.46 (s, 1H, Ar), 7.70 (d, 1H, J=1.7 Hz, Ar), 7.61 (d, 1H, 8.0 Hz, Ar), 7.42 (dd, 1H, J=8.6, 1.8 Hz, Ar), 3.87 (q, 1H, J=7.1 Hz, CHCH3), 1.51 (d, 3H, J=7.1 Hz, CHCH3).

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane
  2. customthe combined organic phases were dried
  3. filtrationfiltered over magnesium sulphate
  4. customThe solvent was removed in a vacuum
  5. customthe residue was purified by column chromatography (SiO2, dichloromethane/MeOH=15:1)

Sources & evidence

ORD record
ord-f3c1799803cd4009bcce601d591c79b5
Source dataset
uspto-grants-2012_12
Patent number
US08334315B2

Reaction notes

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