Lithium Hydroxide → HCID 21876352, compound

HRID 967847Notes

Reaction equation

HRID 967847 reaction equation
C([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[CH2:23][CH3:24])=[CH:10][CH:9]=1)(=O)CC.[Li+].[OH-]>CO.C1COCC1>[CH2:23]([C:15]1[N:14]([C:11]2[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][OH:5])=[CH:13][CH:12]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=1)[CH3:24]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 21876330HCID 21876330, compound

Product 1

HCID 21876352HCID 21876352, compoundYield 86,356.602%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 2-[4-(2-ethyl-1H-benzimidazol-1-yl)phenyl]ethyl propionate (1.3 g, 4 mmol) in methanol/THF (v/v, 1:1, 32 mL) was added 4N aqueous LiOH (8 mL, 8 mmol) and the resulting mixture was stirred at room temperature. After 3 h, the mixture was concentrated. The residue was dissolved in water (30 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with brine (50 mL), dried (MgSO4), and concentrated. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 2:1 to 0:1) to afford 920 g (86%) of the title compound as pale brown solids: 1H-NMR (CDCl3)δ1.26 (3H, t, J=7.5 Hz), 2.80 (2H, q, J=7.5 Hz), 3.00 (2H, t, J=6.5 Hz), 3.98 (2H, t, J=6.5 Hz), 7.25-7.08 (3H, m), 7.31 (2H, d, J=8.3 Hz), 7.45 (2H, d, J=8.3 Hz), 7.81-7.75 (1H, m).

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionThe residue was dissolved in water (30 mL)
  3. extractionextracted with ethyl acetate (100 mL)
  4. washThe organic layer was washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 2:1 to 0:1)

Sources & evidence

ORD record
ord-e053c9d7a574417e9db50c200c4b8283
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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