Methanol → HCID 12870475, compound

HRID 223669Notes

Reaction equation

HRID 223669 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)=O)C.CO.O>C1(C)C=CC=CC=1>[CH:14]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)=[O:13]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 12870392Ethyl 6-(1H-imidazol-1-yl)hexanoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 12870475HCID 12870475, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Under an atmosphere of nitrogen, 8.8 ml of a 25%(W/V) solution of diisobutylaluminium hydride in toluene was added dropwise to a solution of 2.50 g of 1-(5-ethoxycarbonylpentyl)imidazole in 120 ml of toluene at -70° C., and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture was added one ml of methanol at -70° C., and one ml of water at 0° C., then the mixture was stirred at 30° C. for one hour. The reaction mixture was filtered, the filtrate was dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of chloroform and methanol (25:1) as eluent to give 1.15 g of the title compound having the following physical characteristics:

Workup

  1. filtrationThe reaction mixture was filtered
  2. dry with materialthe filtrate was dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel using
  5. additiona mixture of chloroform and methanol (25:1) as eluent

Sources & evidence

ORD record
ord-736e2cb90f504f6f99fa617de5e1be61
Source dataset
uspto-grants-1982_10
Patent number
US04355170

Reaction notes

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