Methyl Acrylate → 4,5-Dihydro-5-(methoxycarbonyl)-3-isoxazolepropanoic acid methyl ester

HRID 653398

反応式

HRID 653398 の反応式
[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH2:5][CH2:6][N+:7]([O-:9])=O.[C:11]([O:15][CH3:16])(=[O:14])[CH:12]=[CH2:13].C(N(CC)CC)C.C1(N=C=O)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:16][O:15][C:11](=[O:14])[CH2:12][CH2:13][C:6]1[CH2:5][CH:4]([C:3]([O:2][CH3:1])=[O:10])[O:9][N:7]=1

参加物

6

反応物 4

HCID 7294Methyl AcrylateHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 25604Methyl 4-nitrobutyrate

生成物 1

HCID 139115534,5-Dihydro-5-(methoxycarbonyl)-3-isoxazolepropanoic acid methyl ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 23.8 g of 4-nitrobutyric acid methyl ester (made in accordance with Bruson, U.S. Pat. No. 2,342,119) 39.6 g of methyl acrylate, 0.2 g triethyl amine in 200 ml of toluene is stirred and treated dropwise with 23.8 g of phenyl isocyanate. The mixture is stirred for 72 hours at room temperature and heated at 90° C. for two hours. The mixture is cooled, filtered to remove the diphyl urea, and concentrated under reduced pressure. The resulting oil is chromatographed on SiO2 (elution with hexane:ethyl-acetate; 75:25) to yield 4,5-dihydro-5-(methoxycarbonyl)-3-isoxazolepropanoic acid methyl ester as a colorless oil. NMR (CDCl3) and 4.93 (t, J=9 Hz, 1H), 3.72 (s, 3H), 3.63 (s, 3H), 3.20 (d, J-9 Hz, 2H9, 2.61 (s, 4H). IR (KBr) 2956, 2851, 1739, 1632, 1439, 1367, 1340, 1215. IR (cm-1).

後処理

  1. temperatureheated at 90° C. for two hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. customto remove the diphyl urea
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oil is chromatographed on SiO2 (elution with hexane:ethyl-acetate; 75:25)

出典と根拠

ORDレコード
ord-39b3ead62885473aac7b69884bfc2550
出典データセット
uspto-grants-1987_06
特許番号
US04677098

関連ノート

読み込み中…