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

HRID 42790Notes

Reaction equation

HRID 42790 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+N+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-87cb10e7f33c4064a287868b45ca0765
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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