Triethylamine → 3-Phenethyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester

HRID 972078Notes

Reaction equation

HRID 972078 reaction equation
[C:1]([OH:6])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[CH2:7](N1CCC(=O)C1)[CH3:8].[N+:15]([CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([O-:17])=O.C(N(CC)CC)C.P(Cl)(Cl)(Cl)=O>C(Cl)(Cl)Cl>[CH2:7]([O:5][C:1]([C:2]1[C:18]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:15][O:17][C:3]=1[CH3:4])=[O:6])[CH3:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 5623331-Nitro-3-phenylpropaneHCID 70608345Ethyl-3-pyrrolidone crotonate

Product 1

HCID 538657393-Phenethyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of 48.5 g. (0.265 mole) ethyl-3-pyrrolidone crotonate 48.2 g. (0.291 mole) 1-nitro-3-phenylpropane and 208 ml. (1.490 mole) triethylamine in 500 ml. chloroform is cooled to 0° and treated by the dropwise addition of 44.6 g. (0.291 mole) phosphorous oxychloride in 105 ml. chloroform. The addition takes approximately three hours and the temperature is maintained at about 0°±5°. After the addition the mixture is stirred at room temperature over night. The resulting mixture is then washed once with cold water, three times with 6 N hydrochloric acid, once with 1 N sodium hydroxide and once with saturated sodium chloride. The organic layer is dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue is distilled and the fraction collected at about 145°-150°/0.45 mm to give 3-phenethyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester. Identified by NMR and IR.

Workup

  1. additionA mixture of 48.5 g
  2. additiontreated by the dropwise addition of 44.6 g
  3. additionThe addition
  4. temperaturethe temperature is maintained at about 0°±5°
  5. additionAfter the addition the mixture
  6. washThe resulting mixture is then washed once with cold water, three times with 6 N hydrochloric acid, once with 1 N sodium hydroxide and once with saturated sodium chloride
  7. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. distillationThe residue is distilled
  11. customthe fraction collected at about 145°-150°/0.45 mm

Sources & evidence

ORD record
ord-f0ef3c5c2e3b48069e37212a1aabb915
Source dataset
uspto-grants-1979_07
Patent number
US04163057

Reaction notes

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