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

HRID 1643520ノート

反応式

HRID 1643520 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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, 2 H); ESIMS: m/z 374 (M−H).

後処理

  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)

出典と根拠

ORDレコード
ord-eaf9d19fec8242ee8247ec5b630a461a
出典データセット
uspto-grants-2012_02
特許番号
US08119819B2

反応ノート

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