Acetic Acid → HCID 20358652, compound

HRID 1626837Notes

Reaction equation

HRID 1626837 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].O[Li].O.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 168937Lithium hydroxide, monohydrateHCID 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 (425 mg, 2.07 mmol) was dissolved in THF (8 ml) and water (8 ml). LiOH.H2O (93 mg, 2.21 mmol) was added thereto at RT. The reaction mixture was stirred for 40 h at RT, combined with water (25 ml) and adjusted with acetic acid to a pH value of 3. The reaction mixture was extracted with DC M and the combined organic phases were dried over MgSO4 and filtered. The solvent was removed under a vacuum and the residue purified by means of column chromatography (n-hexane/MeOH=15:1).

Workup

  1. customat RT
  2. extractionThe reaction mixture was extracted with DC M
  3. dry with materialthe combined organic phases were dried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed under a vacuum
  6. customthe residue purified by means of column chromatography (n-hexane/MeOH=15:1)

Sources & evidence

ORD record
ord-1142d829c5db4727821893bfd91ab038
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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