Red-Al → HCID 178519947, compound

HRID 241039Notes

Reaction equation

HRID 241039 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13](OCC)=[O:14])[NH:11][CH:12]=2)=[CH:4][CH:3]=1.COCCO[AlH2-]OCCOC.[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH2:13][OH:14])[NH:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 16684438Red-AlHCID 178470172HCID 178470172, compound

Product 1

HCID 178519947HCID 178519947, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 4-(4-bromophenyl)-1H-imidazole-2-carboxylate (1.30 g, 4.40 mmol) in THF (30 mL) was slowly added Red-Al (65 wt % in toluene, 2.0 mL, 6.16 mmol) at −25° C. The reaction mixture was stirred for 4 h at the same temperature then slowly warmed to 0° C. over 1 h and quenched with 20% sodium tartrate solution (30 mL). The reaction was extracted with ethyl acetate (70 mL) and the organic layer was left for 3 h at room temperature. A solid separated and was collected by filtration, washed with ethyl acetate and dried to afford (4-(4-bromophenyl)-1H-imidazol-2-yl)methanol (778 mg, 71.0%). MS (EI) for C10H9BrN2O: 254.1 (MH+).

Workup

  1. customat −25° C
  2. customquenched with 20% sodium tartrate solution (30 mL)
  3. extractionThe reaction was extracted with ethyl acetate (70 mL)
  4. waitthe organic layer was left for 3 h at room temperature
  5. customA solid separated
  6. filtrationwas collected by filtration
  7. washwashed with ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-4869bba2920d4911a0a45af237840930
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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