Sodium sulfate decahydrate → [1-(4-fluorophenyl)-1H-imidazol-5-yl]methanol

HRID 30622

Reaction equation

HRID 30622 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13](OCC)=[O:14])=[CH:11][N:10]=[CH:9]2)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[CH:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21225700DiisobutylaluminumhydrideHCID 55563221Ethyl 1-(4-fluorophenyl)imidazole-5-carboxylate

Product 1

HCID 69209067[1-(4-fluorophenyl)-1H-imidazol-5-yl]methanolYield 53.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 1-(4-fluorophenyl)-1H-imidazole-5-carboxylate (9.37 g) in tetrahydrofuran (100 ml) was added dropwise diisobutylaluminum hydride (1.5 mol/l toluene solution, 60 ml) at 0° C. The mixture was stirred at 0° C. for 1 hr., sodium sulfate decahydrate (13.0 g) was added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered, and the organic layer was concentrated to give [1-(4-fluorophenyl)-1H-imidazol-5-yl]methanol (4.10 g, 53%) as crystals. Recrystallization thereof from ethyl acetate-isopropyl ether gave pale-yellow prism crystals. melting point: 96-98° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-8ba9733e0fdc485da6271498d954698d
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

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