Ethanol → Ethyl 5-methylisoxazole-4-carboxylate

HRID 329778Notes

Reaction equation

HRID 329778 reaction equation
Cl.[NH2:2]O.[OH-].[Na+].C(OC=C[C:11](=O)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])C.NO.[CH2:21]([OH:23])[CH3:22]>O>[CH3:22][C:21]1[O:23][N:2]=[CH:11][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

7

Reactant 5

HCID 702Ethanol2×HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 54463595Ethyl ethoxymethyleneacetoacetate

Product 1

HCID 7009317Ethyl 5-methylisoxazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Hydroxylamine hydrochloride (52.6 g) was dissolved in water (150 ml) and stirred while an ice-cold solution of sodium hydroxide (30.28 g) in water (100 ml) was added. This solution was stirred for 15 minutes then absolute ethanol (600 ml) added and the solution stirred for a further 15 minutes. Ethyl ethoxymethyleneacetoacetate (128 g) was dissolved in absolute ethanol (100 ml) and added to the hydroxylamine solution. After stirring for 30 hours the solvents were removed on a rotary evaporator (bath at 45° C.). The clear oil was distilled at reduced pressure through a 15 cm Vigreaux column. Product collected as a clear oil at 50°-54° C./0.5 mm Hg.

Workup

  1. additionwas added
  2. stirringthe solution stirred for a further 15 minutes
  3. stirringAfter stirring for 30 hours the solvents
  4. customwere removed on a rotary evaporator (bath at 45° C.)
  5. distillationThe clear oil was distilled at reduced pressure through a 15 cm Vigreaux column
  6. customProduct collected as a clear oil at 50°-54° C./0.5 mm Hg

Sources & evidence

ORD record
ord-cda71459fbe04a208c42c0e26b0d78c1
Source dataset
uspto-grants-1990_01
Patent number
US04892963

Reaction notes

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