Aluminium lithium hydride → HCID 178519842, compound

HRID 2368476Notes

Reaction equation

HRID 2368476 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13](N(OC)C)=[O:14])=[CH:11][N:10]=[C:9]2[SH:19])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH:13]=[O:14])=[CH:11][N:10]=[C:9]2[SH:19])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178502684HCID 178502684, compound

Product 1

HCID 178519842HCID 178519842, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(4-fluorophenyl)-2-mercapto-N-methoxy-N-methyl-1H-imidazole-5-carboxamide (8) (1 g, 3.55 mmol) in anhydrous THF (71 mL) at 0° C. was added lithium aluminum hydride (2M in THF, 5.3 mL, 10.65 mmol). The reaction was stirred at 0° C. for 1 h and for an additional 3 h at room temperature. The reaction was quenched at 0° C. with 15% sodium bicarbonate (40 mL) and water (40 mL) and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-100% EtOAc in hexanes) to afford 1-(4-fluorophenyl)-2-mercapto-1H-imidazole-5-carbaldehyde (12).

Workup

  1. customThe reaction was quenched at 0° C. with 15% sodium bicarbonate (40 mL) and water (40 mL)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-88884bbf4a0d4d2080cdae6e6ad65096
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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