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Heptane → 3-(2-Chloro-4-methoxy-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol

HRID 1095875
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HRID 1095875 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:20])[C:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=1)=[O:12].[F:21][C:22]([Si](C)(C)C)([F:24])[F:23].O.O.O.[F-].C[N+](C)(C)C.CCCCCCC>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:20])[C:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=1)([OH:12])[C:22]([F:24])([F:23])[F:21]
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참가 물질

6

반응물 4

HCID 8900HeptaneHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2735143Tetramethylammonium fluoride trihydrate2회HCID 86645943HCID 86645943, 화합물

생성물 1

HCID 574212633-(2-Chloro-4-methoxy-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol수율 76.7%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
4회

실험 절차

To a solution of 2-(2-chloro-4-methoxy-phenyl)-1-(2-chloro-pyridin-4-yl)-propan-1-on (14.75 g, 0.0475 mol) in tetrahydrofuran (900 ml) was added a solution of (trifluoromethyl)-trimethylsilane (14.89 g, 0.104 mol) in tetrahydrofuran (100 ml) at 0° C. (duration: 5 min.). Tetramethylammonium fluoride trihydrate 1M in THF (4.76 ml, 4.76 mmol) was added and the mixture was stirred at r.t. for 3 h. A second portion of Tetramethylammonium fluoride trihydrate 1M in THF (4.76 ml, 4.47 mmol) was added and the mixture was stirred at r.t. for 1 h. The mixture was poured in ice water and extracted twice with AcOEt. The organic phases were washed with saturated aqueous NaHCO3 solution and brine, dried over MgSO4, filtered and concentrated to give an oil, which solidified over night. The residue was treated with heptane, filtered off and dried to give the title compound (13.85 g) as a light yellow crystalline product. MS (m/e, ISP neg. ion)=378.4 [M−H+].

후처리

  1. stirringthe mixture was stirred at r.t. for 1 h
  2. extractionextracted twice with AcOEt
  3. washThe organic phases were washed with saturated aqueous NaHCO3 solution and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil, which
  8. waitsolidified over night
  9. filtrationfiltered off
  10. customdried

출처 및 근거

ORD 기록
ord-1981f0450a194d0f8abf6b000e33de96
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08138189B2

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