Ethyl Acetate → HCID 66619327, compound

HRID 417133Notes

Reaction equation

HRID 417133 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:14](O)=[O:15])[C:11]3[CH:23]=[C:24]([F:28])[C:25]([F:27])=[CH:26][C:10]=3[N:9]=2)=[C:4]([CH3:29])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].C(OCC)(=O)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[CH2:14][OH:15])[C:11]3[CH:23]=[C:24]([F:28])[C:25]([F:27])=[CH:26][C:10]=3[N:9]=2)=[C:4]([CH3:29])[CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 66619270[2-(4-Chloro-2-methyl-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acid

Product 1

HCID 66619327HCID 66619327, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.94 g (2.244 mmol) [2-(4-chloro-2-methyl-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acid in 15 ml dry tetrahydrofuran was added 98 mg (2.356 mmol) lithium aluminum hydride at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 2 hours. The reaction mixture was poured on 50 ml 10% aqueous sodium potassium tartrate solution and 50 ml ethyl acetate. The layers were separated and the aqueous layers were extracted again with 50 ml ethyl acetate. The combined organic layers were washed with 50 ml brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 60:40) to give the title compound as a light yellow solid (57%). MS (Turbo Spray): m/z=405.4 [M+H].

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layers were extracted again with 50 ml ethyl acetate
  3. washThe combined organic layers were washed with 50 ml brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 60:40)

Sources & evidence

ORD record
ord-2dbef34f074e4f73be5b35f035dfa703
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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