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

HRID 1795025노트

반응식

HRID 1795025 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-113f9c1f7be64082b02382b2c3f7e41a
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07026321B2

반응 노트

불러오는 중…