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

HRID 913717

반응식

HRID 913717 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-0bdb63be9cc6459fafce5c6cd285e8e6
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026262B2

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