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

HRID 417061
Notes
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Reaction equation

HRID 417061 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

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].

Workup

  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)

Sources & evidence

ORD record
ord-f725c64409ad48168e319466e22cb300
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08088930B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes