Tetrahydrofuran → 3-(1-Trityl-1H-imidazol-4-YL)propan-1-OL

HRID 1067658Notes

Reaction equation

HRID 1067658 reaction equation
[C:1]1([C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:8]2[CH:12]=[C:11](CCCC(OCC)=O)[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+].[CH2:46]1C[O:49][CH2:48][CH2:47]1>C(OCC)(=O)C>[C:27]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:8]2[CH:12]=[C:11]([CH2:46][CH2:47][CH2:48][OH:49])[N:10]=[CH:9]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24436Sodium SulfateHCID 11568047HCID 11568047, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 108328403-(1-Trityl-1H-imidazol-4-YL)propan-1-OL

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The above ester (7.5 g; 18.3 mmol), dissolved in freshly distilled THF (75 ml), is added dropwise to a solution of 0.8 g of lithium aluminium hydride (21 mmol) in freshly distilled THF (45 ml) in the cold and with stirring. Stirring is continued at room temperature for 12 hours, and the lithium aluminium hydride is then decomposed by adding saturated sodium sulphate solution dropwise. The resulting complex is filtered off, and the THF is dried over magnesium sulphate, giving an oil which is reduced in ethyl acetate to give 1-(triphenylmethyl)-4-(3-hydroxypropyl)-1H-imidazole in the form of a white powder (5.8 g; 87%); m.p.: 130° C.

Workup

  1. stirringStirring
  2. filtrationThe resulting complex is filtered off
  3. dry with materialthe THF is dried over magnesium sulphate
  4. customgiving an oil which

Sources & evidence

ORD record
ord-36f1bfb3c3324d15a02ebd36f206e6bb
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Reaction notes

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