Triethylamine → (4-Chloro-phenyl)-[5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-4,5-dihydroisoxazol-3-yl]methanone

HRID 2113241노트

반응식

HRID 2113241 반응식
[CH:1]1[C:6]([C:7](/[C:9](/Cl)=[N:10]/[OH:11])=[O:8])=[CH:5][CH:4]=[C:3]([Cl:13])[CH:2]=1.[F:14][C:15]([F:25])([F:24])[C:16]([C:20]([F:23])([F:22])[F:21])([OH:19])[CH:17]=[CH2:18].C(N(CC)CC)C>C1COCC1>[Cl:13][C:3]1[CH:4]=[CH:5][C:6]([C:7]([C:9]2[CH2:18][CH:17]([C:16]([OH:19])([C:15]([F:24])([F:14])[F:25])[C:20]([F:21])([F:23])[F:22])[O:11][N:10]=2)=[O:8])=[CH:1][CH:2]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 37879581,1,1-Trifluoro-2-(trifluoromethyl)but-3-en-2-olHCID 9614280(1Z)-2-(4-chlorophenyl)-N-hydroxy-2-oxoethanimidoyl chloride

생성물 1

HCID 57644093(4-Chloro-phenyl)-[5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-4,5-dihydroisoxazol-3-yl]methanone수율 28.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of commercially available 4-chlorophenyl glyoxylohydroxamyl chloride (218 mg, 1 mmol) in 1,1,1-trifluoro-2-trifluoromethyl-but-3-en-2-ol (2 mmol) was added a solution of triethylamine (111 mg, 1.1 mmol) in THF (10 ml) dropwise by syringe pump at r.t. over 30 h. The mixture was concentrated under reduced pressure and diluted with EtOAc. The organic layer was washed with 1N HCl, H2O and dried over MgSO4. Solvent was evaporated under reduced pressure and the residue was purified by preparative TLC (Hexanes:EtOAc, 4:1) to afford the title compound as a white solid (107.3 mg). 1H NMR δ 3.54 (s, 1H), 3.60 (dd, 1H), 3.76 (dd, 1H), 5.12 (t, 1H), 7.45 (d, 2H), 8.14 (d, 2H); ESIMS: m/z 374 (M−H).

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with 1N HCl, H2O
  4. dry with materialdried over MgSO4
  5. customSolvent was evaporated under reduced pressure
  6. customthe residue was purified by preparative TLC (Hexanes:EtOAc, 4:1)

출처 및 근거

ORD 기록
ord-51eb1b18e45b4729a469aff375039470
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07524969B2

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