Water → 3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-5-[3,5-bis(trifluoromethyl)phenyl]isoxazole

HRID 913717

反応式

HRID 913717 の反応式
[N+:1]([CH2:4][CH2:5][O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)([O-:3])=O.[C:13]([C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=1)#[CH:14].N(C1C=CC=CC=1)=C=O.O>C(#N)C>[O:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]1[O:6][CH2:5][C:4]1[CH:14]=[C:13]([C:15]2[CH:16]=[C:17]([C:25]([F:26])([F:27])[F:28])[CH:18]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:20]=2)[O:3][N:1]=1

参加物

6

反応物 4

HCID 962WaterHCID 7672Phenyl isocyanateHCID 15126071-Ethynyl-3,5-bis(trifluoromethyl)benzeneHCID 37486562-(2-Nitroethoxy)tetrahydropyran

生成物 1

HCID 578004293-[(tetrahydro-2H-pyran-2-yloxy)methyl]-5-[3,5-bis(trifluoromethyl)phenyl]isoxazole収率 41%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

To a solution of 2-[(2-nitroethyl)oxy]tetrahydro-2H-pyran (483 μL, 3.15 mmol) and 1-ethynyl-3,5-bis(trifluoromethyl)benzene (3.0 g, 12.6 mmol) in dry acetonitrile (15 mL) were added TEA (4.4 ml, 31.5 mmol) and isocyanatobenzene (3.4 mL, 31.5 mmol) at rt. The reaction is stirred at 50° C. for 5 h. Water was added and the mixture was extracted with Et2O three times. The combined organic layers were then washed with brine once, dried over MgSO4 and concentrated in vacuo. The residue was purified by radial chromatography (0-40% EtOAc-hexanes gradient) to afford the title compound (0.51 g, 41% yield): MS (ES) m/z 418 (M+Na+).

後処理

  1. extractionthe mixture was extracted with Et2O three times
  2. washThe combined organic layers were then washed with brine once
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by radial chromatography (0-40% EtOAc-hexanes gradient)

出典と根拠

ORDレコード
ord-0bdb63be9cc6459fafce5c6cd285e8e6
出典データセット
uspto-grants-2011_09
特許番号
US08026262B2

関連ノート

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