Hydrochloric Acid → HCID 61397610, compound

HRID 58527Notes

Reaction equation

HRID 58527 reaction equation
Br[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([O:10]CC)=[O:9])[CH:4]=1.[OH-].[Na+].Cl.[CH2:16]([OH:18])[CH3:17]>>[CH2:16]([O:18][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([OH:10])=[O:9])[CH:4]=1)[CH3:17]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 13124955Ethyl 5-(bromomethyl)-1,2-oxazole-3-carboxylate

Product 1

HCID 61397610HCID 61397610, compoundYield 38%

Procedure

To an oily suspension of ethyl 5-(bromomethyl)isoxazole-3-carboxylate (0.680 g; 2.91 mmol) in aqueous 1M sodium hydroxide (6.4 mL; 6.4 mmol) was added 1 mL of ethanol. The oily suspension immediately transformed to a white solid suspension. The mixture was stirred overnight at room temperature. The pH of the solution was adjusted between 2 and 3 by addition of 6N hydrochloric acid. The solution was extracted with ethyl acetate. Organic extracts were dried over magnesium sulfate and evaporated to afford 0.189 g (38%) of 5-(ethoxymethyl)isoxazole-3-carboxylic acid as a white solid, which was directly used in the next step.

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. dry with materialOrganic extracts were dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-2317ed92cd61422787136119e01062ab
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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