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

HRID 1643522ノート

反応式

HRID 1643522 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])[C:17]#[CH:18].C(N(CC)CC)C>C1COCC1>[Cl:13][C:3]1[CH:4]=[CH:5][C:6]([C:7]([C:9]2[CH:18]=[C: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 9614280(1Z)-2-(4-chlorophenyl)-N-hydroxy-2-oxoethanimidoyl chlorideHCID 136678281,1,1-Trifluoro-2-trifluoromethyl-but-3-yn-2-ol

生成物 1

HCID 10156217(4-Chloro-phenyl)-[5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-isoxazol-3-yl]methanone収率 46.7%

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 (109 mg, 0.5 mmol) in 1,1,1-trifluoro-2-trifluoromethyl-but-3-yn-2-ol from step 1 (about 1 mmol) was added a solution of triethylamine (60 mg, 0.6 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, 5:1) to afford the title compound as a white solid (87.2 mg). 1H NMR (DMSO-d6) δ 7.37 (s, 1H), 7.60 (d, 2 H), 8.14 (d, 2H), 9.92 (s, 1H); ESIMS: m/z 372 (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, 5:1)

出典と根拠

ORDレコード
ord-bf1ba5b9a1ff4a2ea587f54d927bb5aa
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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