Dimethylformamide → HCID 22064722, compound

HRID 1828117Notes

Reaction equation

HRID 1828117 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[CH:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CN([CH:28]=[O:29])C.[NH4+].[Cl-]>C1COCC1>[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[CH:28]=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 22064730HCID 22064730, compoundHCID 178418339Butyllithium

Product 1

HCID 22064722HCID 22064722, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-75 °C

Procedure

To a stirred, cooled (−75° C.) light orange solution of 3.79 g 1-(2-benzyloxy-ethyl)-1H-benzoimidazole in 80 ml THF under argon atmosphere was added dropwise 9.4 ml n-butyllithium solution (1.6 M in hexanes) for 15 min (temperature of the solution below −71° C. during the addition; reaction mixture turning to orange). When addition was complete, stirring at −75° C. was continued for 1 h 30. The reaction mixture was then treated with 1.44 ml DMF within 5 min and stirring at −75° C. was continued for 4 h. Then 40 ml of saturated NH4Cl-solution was added to the reaction mixture which was subseqently allowed to warm to r.t. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated. The crude product was purified by chromatography on silica gel using a gradient from cyclohexane to cyclohexane/EtOAc 65:35 to give 1.09 g 1-(2-benzyloxy-ethyl)-1H-benzoimidazole-2-carbaldehyde as viscous yellow oil. MS 281.0 ([M+H]+)

Workup

  1. additionduring the addition
  2. customreaction mixture
  3. additionWhen addition
  4. stirringstirring at −75° C.
  5. waitwas continued for 4 h
  6. temperatureto warm to r.t
  7. washThe organic phase was washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was purified by chromatography on silica gel using a gradient from cyclohexane to cyclohexane/EtOAc 65:35

Sources & evidence

ORD record
ord-1063eb401dc3498ab6a73ec94a8d0c1d
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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