Triethylamine → Ethyl 5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole-3-carboxylate

HRID 1795025

反応式

HRID 1795025 の反応式
[CH2:1]([O:3][C:4](=[O:9])[C:5](Cl)=[N:6][OH:7])[CH3:2].[F:10][C:11]([F:21])([F:20])[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[CH2:17])=[CH:14][CH:13]=1.C(N(CC)CC)C>O1CCCC1>[F:10][C:11]([F:20])([F:21])[C:12]1[CH:13]=[CH:14][C:15]([CH:16]2[O:7][N:6]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:9])[CH2:17]2)=[CH:18][CH:19]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27827981-Ethenyl-4-(trifluoromethyl)benzeneHCID 6816376Ethyl chloro(hydroximino)acetate

生成物 1

HCID 22064077Ethyl 5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole-3-carboxylate収率 88.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred mixture of 2-chloro-2-hydroxyiminoacetic acid ethyl ester (2.11 g, 13.52 mmol) and 4-trifluoromethystyrene (2.0 g, 11.27 mmol) in anhydrous tetrahydrofuran (15 ml) was added dropwise a solution of triethylamine (3.0 ml, 21.52 mmol) in tetrahydrofuran (5 ml) at room temperature. The resulting reaction mixture was stirred at an atmosphere of nitrogen for 16 hours, filtered, partitioned between water and ethyl acetate (2×50 ml), washed with saturated aqueous sodium bicarbonate, 30% aqueous ammonium chloride, brine, dried over sodium sulfate, and concentrated to afford a pale yellow solid, which was purified by chromatography (2:8 EtOAc:Hexane) to afford ethyl 5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole-3-carboxylate (2.86 g, M+1=288.2)

後処理

  1. customThe resulting reaction mixture
  2. filtrationfiltered
  3. custompartitioned between water and ethyl acetate (2×50 ml)
  4. washwashed with saturated aqueous sodium bicarbonate, 30% aqueous ammonium chloride, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto afford a pale yellow solid, which
  8. customwas purified by chromatography (2:8 EtOAc:Hexane)

出典と根拠

ORDレコード
ord-113f9c1f7be64082b02382b2c3f7e41a
出典データセット
uspto-grants-2006_04
特許番号
US07026321B2

関連ノート

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