Methanol → 2-[4-(Hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylic acid

HRID 1716859Notes

Reaction equation

HRID 1716859 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([C:14]([O:16]CC)=[O:15])[N:13]=2)=[CH:5][CH:4]=1.CO.C1COCC1.[Li+].[OH-]>O>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[N:13]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 46834789Ethyl 2-[4-(hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylate

Product 1

HCID 575501932-[4-(Hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ethyl 2-[4-(hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylate (2.5 g, 10.1 mmol) in 1:1 MeOH:THF was treated with 1.0 M LiOH:H2O and stirred at room temperature overnight and concentrated in in vacuo. The resulting residue was diluted with water, treated with 1.0 M HCl and filtered to afford the title product 91% yield, identified by NMR and mass spectral analyses. LCMS (ESI+) 219 (MH+).

Workup

  1. concentrationconcentrated in in vacuo
  2. additionThe resulting residue was diluted with water
  3. additiontreated with 1.0 M HCl
  4. filtrationfiltered

Sources & evidence

ORD record
ord-6a72186a4c8346eea6a8aa93cb2b02fb
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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