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

HRID 1827887노트

반응식

HRID 1827887 반응식
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH2:10])=[CH:5][CH:4]=1.Cl[CH:14]([NH:20][OH:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(N(CC)CC)C>C1COCC1>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[O:21][N:20]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]2)=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27827981-Ethenyl-4-(trifluoromethyl)benzeneHCID 22064134Ethyl 2-chloro-2-(hydroxyamino)acetate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a mixture of 1-(trifluoromethyl)-4-vinylbenzene (2.0 g, 11.27 mmol), a compound of formula (20) and ethyl 2-chloro-2-(hydroxyamino)acetate (2.11 g, 13.52 mmol), a compound of formula (21), in anhydrous THF was added a solution of triethylamine (3.0 ml) in tetrahydrofuran was added dropwise at room temperature. The mixture was stirred overnight under N2. The white precipitate thus formed was filtered off, and washed twice with tetrahydrofuran (10 ml). The solvent was removed from the filtrate under reduced pressure, and the residue partitioned between water/ethyl acetate (20 ml:20 ml v/v), extracting three times with 20 ml of ethyl acetate. The combined organic layers were washed with aqueous ammonium chloride, and dried over MgSO4, to provide ethyl 5-[4-(trifluoromethyl)phenyl]-4,5-dihydroisoxazole-3-carboxylate, a compound of formula (22).

후처리

  1. additionwas added dropwise at room temperature
  2. customThe white precipitate thus formed
  3. filtrationwas filtered off
  4. washwashed twice with tetrahydrofuran (10 ml)
  5. customThe solvent was removed from the filtrate under reduced pressure
  6. customthe residue partitioned between water/ethyl acetate (20 ml:20 ml v/v)
  7. extractionextracting three times with 20 ml of ethyl acetate
  8. washThe combined organic layers were washed with aqueous ammonium chloride
  9. dry with materialdried over MgSO4

출처 및 근거

ORD 기록
ord-4fa9d205e4504e8882f4f8c13f3d8b56
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07056924B2

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