Hydrochloric Acid → 5-(3-Hydroxymethyl-phenyl)-oxazole-4-carboxylic acid

HRID 2065007Notes

Reaction equation

HRID 2065007 reaction equation
N#N.C[O:4][C:5]([C:7]1[N:8]=[CH:9][O:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][OH:19])[CH:13]=1)=[O:6].[OH-].[Na+].Cl>C1COCC1>[OH:19][CH2:18][C:14]1[CH:13]=[C:12]([C:11]2[O:10][CH:9]=[N:8][C:7]=2[C:5]([OH:6])=[O:4])[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 14798Sodium HydroxideHCID 669288325-(3-Hydroxymethyl-phenyl)-oxazole-4-carboxylic acid methyl ester

Product 1

HCID 669283575-(3-Hydroxymethyl-phenyl)-oxazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(3-hydroxymethyl-phenyl)-oxazole-4-carboxylic acid methyl ester (265 mg, 1.13 mmol) in THF (11.0 mL) was treated with a 1N NaOH (5.5 mL). The resulting mixture was stirred for 1.5 h then acidified with 1N HCl, extracted twice with EA (2×25 mL) and the combined organic phases were washed with brine (10 mL). The organic layer was dried over MgSO4, filtered, and the solvent removed under reduced pressure to give the title compound as a white solid. LC-MS-conditions 02: tR=0.67 min, [M+AcCN+H]+=261.29.

Workup

  1. extractionextracted twice with EA (2×25 mL)
  2. washthe combined organic phases were washed with brine (10 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a6f1187df68a46f2940ce650982ad227
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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