Sodium Hydroxide → HCID 11256556, compound

HRID 1661891Notes

Reaction equation

HRID 1661891 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:29][CH3:30])=[CH:20][CH:21]=[C:22]([C:23]#[C:24][Si](C)(C)C)[C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:23]([C:22]1[C:12]2[N:11]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=3)[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]=2[C:19]([O:29][CH3:30])=[CH:20][CH:21]=1)#[CH:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57772017HCID 57772017, compound

Product 1

HCID 11256556HCID 11256556, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 17 mg (0.04 mmol) 2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-4-trimethylsilanylethynyl-1H-benzoimidazole and 0.5 ml 1N NaOH in 2 ml THF/methanol (1:1) is stirred for 1 hour at 60° C. The reaction mixture is cooled to room temperature and poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified on 0.5 mm silica gel plates (hexane:EtOAc=3:1) to afford 7 mg of the title compound as yellow oil.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. additionpoured on water
  3. extractionextracted (3×) with ethyl acetate
  4. washThe combined organic layers are washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified on 0.5 mm silica gel plates (hexane:EtOAc=3:1)

Sources & evidence

ORD record
ord-000ea505fc394a759e7a4acbb7ca8fb9
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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