Water → HCID 10607160, compound

HRID 544970Notes

Reaction equation

HRID 544970 reaction equation
C([O:3][C:4]([C:6]1[NH:7][CH:8]=[N:9][C:10]=1[C:11]([CH3:15])([CH3:14])[CH:12]=[CH2:13])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[CH3:15][C:11]([C:10]1[N:9]=[CH:8][NH:7][C:6]=1[CH2:4][OH:3])([CH3:14])[CH:12]=[CH2:13]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178442315HCID 178442315, compound

Product 1

HCID 10607160HCID 10607160, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-(1,1-dimethyl-allyl)-3H-imidazole-4-carboxylic acid ethyl ester (3.13 g, 15.0 mmol) in THF (60 ml) was added dropwise to a suspension of lithium aluminium hydride (95% suspension, 1.00 g, 25.0 mmol) in THF (40 ml) and the mixture was stirred at room temperature for 4 h. Water was added until the evolution of gas ceased, the mixture was stirred for 10 min, then was filtered through a sintered funnel. The precipitate was washed with THF, then with methanol, the filtrate and washings were combined, evaporated, then freeze-dried to afford [5-(1,1-dimethyl-allyl)-3H-imidazol-4-yl]-methanol (2.56 g, 102%). Residual water was removed by azeotroping with chloroform prior to further reaction. (See Hayashi et al., J. Org. Chem., 65:8402-8405 (2000)).

Workup

  1. stirringthe mixture was stirred for 10 min
  2. filtrationwas filtered through a sintered funnel
  3. washThe precipitate was washed with THF
  4. customevaporated
  5. customfreeze-dried

Sources & evidence

ORD record
ord-2f80cb52958948c19efd414acad97f32
Source dataset
uspto-grants-2011_05
Patent number
US07935704B2

Reaction notes

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