Hydrochloric Acid → HCID 61397610, compound

HRID 1918513Notes

Reaction equation

HRID 1918513 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-afc2815ea0ab4c68af6585a02ecc4c7c
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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