Hydrochloric Acid → 5-(2,2-Dimethyl-propyl)-isoxazole-3-carboxylic acid

HRID 1664231Notes

Reaction equation

HRID 1664231 reaction equation
C([O:3][C:4](=[O:15])/[C:5](/O)=[CH:6]/[C:7](=[O:13])[CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])C.Cl.[NH2:17]O.[OH-].[Na+].Cl>CCO>[CH3:10][C:9]([CH3:12])([CH3:11])[CH2:8][C:7]1[O:13][N:17]=[C:5]([C:4]([OH:3])=[O:15])[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 86626580(Z)-2-Hydroxy-6,6-dimethyl-4-oxo-hept-2-enoic acid ethyl ester

Product 1

HCID 674399885-(2,2-Dimethyl-propyl)-isoxazole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (Z)-2-hydroxy-6,6-dimethyl-4-oxo-hept-2-enoic acid ethyl ester (298.5 g, 1.39 mol) in EtOH (1600 ml) is added hydroxylamine hydrochloride (106.5 g, 1.53 mol) and the resulting solution is stirred at room temperature for 24 h. 2N aq sodium hydroxide (1740 ml, 3.48 mol) is added to the reaction and the resulting solution is stirred at rt for 2 h. The reaction mixture is acidified with 6N aq hydrochloric acid, concentrated to about 3 L, and extracted with EtOAc (2000 ml). The combined organic layers are washed with brine, dried over magnesium sulfate and concentrated. The resulting solid is washed with ether and dried to afford the product.

Workup

  1. stirringthe resulting solution is stirred at rt for 2 h
  2. concentrationconcentrated to about 3 L
  3. extractionextracted with EtOAc (2000 ml)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. washThe resulting solid is washed with ether
  8. customdried
  9. customto afford the product

Sources & evidence

ORD record
ord-890f4aee993941488d739f71af40035f
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

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