Ethyl Acetate → HCID 66966212, compound

HRID 1515059Notes

Reaction equation

HRID 1515059 reaction equation
C[O:2][C:3]([C:5]1[CH:21]=[CH:20][C:8]2[N:9]=[C:10]([C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:19])[NH:11][C:7]=2[CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].S([O-])([O-])(=O)=O.[Na+].[Na+].C(OCC)(=O)C>C1COCC1.CCOCC>[CH3:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:12]=1[C:10]1[NH:11][C:7]2[CH:6]=[C:5]([CH2:3][OH:2])[CH:21]=[CH:20][C:8]=2[N:9]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 66965285HCID 66965285, compound

Product 1

HCID 66966212HCID 66966212, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2,6-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid methyl ester (930 mg) (Example 1-255, step 1) in THF (10 mL) was added 16.6 mL of a 1M solution of LiAlH4 in ether dropwise. The mixture was stirred at ambient temperature for 18 h then approximately 4 mL of saturated sodium sulfate solution was added dropwide. Ethyl acetate was added to the mixture and the solvent decanted from any insoluble material. The organic solution was dried over sodium sulfate and the solvent was removed under reduced pressure to give [2-(2,6-dimethylphenyl)-3H-benzoimidazol-5-yl]-methanol as a foam.

Workup

  1. customthe solvent decanted from any insoluble material
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-34dcb0d5aadc4ad9bfdb5f544893f414
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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