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Ethyl Acetate → 2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol

HRID 417061
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HRID 417061 반응식
C([O:3][C:4](=O)[CH:5]([N:12]1[C:16]2[CH:17]=[C:18]([F:22])[C:19]([F:21])=[CH:20][C:15]=2[N:14]=[C:13]1[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>O1CCCC1>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:13]2[N:12]([CH:5]([CH:6]3[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]3)[CH2:4][OH:3])[C:16]3[CH:17]=[C:18]([F:22])[C:19]([F:21])=[CH:20][C:15]=3[N:14]=2)=[CH:24][CH:25]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 66619480[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acid ethyl ester

생성물 1

HCID 666193102-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol수율 67%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

실험 절차

To the solution of 1.0 g (2.3 mmol) [2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acid ethyl ester in 20 mL tetrahydrofuran, 88 mg (2.3 mmol) lithium aluminium hydride were added. A slight warming occurred. After 15 min. the reaction mixture was poured on water and ethyl acetate, extracted, the aqueous phase extracted twice with ethyl acetate and the aqueous phase extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate and evaporated. The crude product was purified by silica gel column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 100:40 v/v) to yield the title compound as an off-white solid (67%). MS (Turbo Spray): m/z=391.2 [M+H].

후처리

  1. temperatureA slight warming
  2. extractionextracted
  3. extractionthe aqueous phase extracted twice with ethyl acetate
  4. extractionthe aqueous phase extracted twice with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe crude product was purified by silica gel column chromatography
  9. washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 100:40 v/v)

출처 및 근거

ORD 기록
ord-f725c64409ad48168e319466e22cb300
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08088930B2

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