Aluminium lithium hydride → HCID 86602962, compound

HRID 2067927Notes

Reaction equation

HRID 2067927 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([CH3:20])[N:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])[C:10]=1[CH3:11])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:19][C:13]1[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=1[N:9]1[C:10]([CH3:11])=[C:6]([CH2:4][OH:3])[N:7]=[C:8]1[CH3:20]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68710301HCID 68710301, compound

Product 1

HCID 86602962HCID 86602962, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-(2,4-Difluoro-phenyl)-2,5-dimethyl-1H-imidazole-4-carboxylic acid ethyl ester (0.5 g, 2 mmol) was dissolved in 15 mL dry THF and cooled to 0° C. Lithium aluminum hydride (2.0 mL, 1M in THF, 2 mmol) was added dropwise and stirred for 45 min at 0° C. The reaction mixture was quenched successively with 76 μl water, 76 μl 15% sodium hydroxide and 230 μl water. Sodium sulfate was added, stirred for 10 min, filtered and evaporated to dryness to obtain the desired compound as a white solid (0.39 g, 92%), MS: m/e=239.2 (M+H+).

Workup

  1. customThe reaction mixture was quenched successively with 76 μl water, 76 μl 15% sodium hydroxide and 230 μl water
  2. additionSodium sulfate was added
  3. stirringstirred for 10 min
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-fb45e90a70ac4a7483b5bee35b8edc1b
Source dataset
uspto-grants-2012_10
Patent number
US08293916B2

Reaction notes

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