Lithium hydroxide, monohydrate → 5-Benzyloxazole-2-carboxylic acid

HRID 928370Notes

Reaction equation

HRID 928370 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][N:10]=1)=[O:5])C.O.[OH-].[Li+]>CO.O>[CH2:11]([C:8]1[O:7][C:6]([C:4]([OH:5])=[O:3])=[N:10][CH:9]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 580812265-Benzyl-oxazole-2-carboxylic acid ethyl ester

Product 1

HCID 580813695-Benzyloxazole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 5-Benzyl-oxazole-2-carboxylic acid ethyl ester (0.95 g, 3.5 mmol) and lithiumhydroxide-hydrate (0.73 g, 17.5 mmol) in 20 mL MeOH and 10 mL water was stirred at room temperature for 2 h. The mixture was evaporated in vacuo, extracted with hexane and the aq. layer was acidified with 1 N aq. HCl. After extraction with ethyl acetate, the organic layer was dried over MgSO4, and evaporated to yield the crude product which was used in the next step without further purification. LCMS (method A) RtA=1.350 min; [M+H]+=203.9.

Workup

  1. customThe mixture was evaporated in vacuo
  2. extractionextracted with hexane
  3. extractionAfter extraction with ethyl acetate
  4. dry with materialthe organic layer was dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-bf0b5c7cdcb54ca089cae6e9f4d9d0e0
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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