Aluminium lithium hydride → 2-[2-(4-Chloro-phenyl)-benzoimidazol-1-yl]-2-cyclohexyl-ethanol

HRID 417081Notes

Reaction equation

HRID 417081 reaction equation
C([O:3][C:4](=O)[CH:5]([N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:13]2[N:12]([CH:5]([CH:6]3[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]3)[CH2:4][OH:3])[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66619211[2-(4-Chloro-phenyl)-benzoimidazol-1-yl]-cyclohexyl-acetic acid ethyl ester

Product 1

HCID 666194992-[2-(4-Chloro-phenyl)-benzoimidazol-1-yl]-2-cyclohexyl-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 5.0 g (12.6 mmol) [2-(4-chloro-phenyl)-benzoimidazol-1-yl]-cyclohexyl-acetic acid ethyl ester in 75 mL dry tetrahydrofuran was cooled to 0° C. and 0.5 g (13.3 mmol) lithium aluminium hydride were added. The cooling bath was removed and stirring was continued for 2 h at room temperature. The reaction was poured on 300 mL 10% aqueous sodium-potassium-tartrate solution and 300 mL ethyl acetate. The phases were separated and the aqueous layer extracted with 300 mL ethyl acetate. The combined organic layers were washed with 300 mL brine, dried over magnesium sulfate, filtered and evaporated to give the desired compound as a white foam which was pure enough for the next step. MS (Turbo Spray): m/z=355.2 [M+H].

Workup

  1. customThe cooling bath was removed
  2. additionThe reaction was poured on 300 mL 10% aqueous sodium-potassium-tartrate solution and 300 mL ethyl acetate
  3. customThe phases were separated
  4. extractionthe aqueous layer extracted with 300 mL ethyl acetate
  5. washThe combined organic layers were washed with 300 mL brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-cc8aa02ce00141cdb00baaa817dde854
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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