2-Chloropropane → HCID 15067843, compound

HRID 1534917Notes

Reaction equation

HRID 1534917 reaction equation
Cl[CH:2]([CH3:4])[CH3:3].[Mg].[C:6]1([C:12]2[NH:13][C:14]([CH3:19])=[C:15]([CH:17]=[O:18])[N:16]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1>[C:6]1([C:12]2[NH:13][C:14]([CH3:19])=[C:15]([CH:17]([OH:18])[CH:2]([CH3:4])[CH3:3])[N:16]=2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 63612-ChloropropaneHCID 5462224MagnesiumHCID 135486495-Methyl-2-phenyl-1H-imidazole-4-carbaldehyde

Product 1

HCID 15067843HCID 15067843, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

35 Grams (0.45 mol) of 2-chloropropane was added to 10.8 g (0.45 mol) of magnesium in 100 ml of diethyloxyde. Then 55.8 g (0.3 mol) of 2-phenyl-4-formyl-5-methyl-1H-imidazole in 100 ml of THF were added. At the end of the addition, the mixture was refluxed for 30 minutes and then cooled and poured on ice water. The aqueous layer was extracted twice with 100 ml of diethyl ether. Evaporation of the solvent gave a residue which was recrystallized in ethanol to yield 40 grams of 2-phenyl-4-(1-hydroxy-2-methylpropyl)-5-methyl-1H-imidazole, which melted at 214° C.

Workup

  1. additionAt the end of the addition
  2. temperaturethe mixture was refluxed for 30 minutes
  3. temperaturecooled
  4. additionpoured on ice water
  5. extractionThe aqueous layer was extracted twice with 100 ml of diethyl ether
  6. customEvaporation of the solvent
  7. customgave a residue which
  8. customwas recrystallized in ethanol

Sources & evidence

ORD record
ord-f350b17729fe4ec6b0e94135cf953802
Source dataset
uspto-grants-1992_02
Patent number
US05091428

Reaction notes

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