Imidazole → Ether isohexane

HRID 1636224Notes

Reaction equation

HRID 1636224 reaction equation
N1C=CN=C1.C(=O)([O-])[O-].[Na+].[Na+].[CH:12]1[C:24]2[CH:23](CC3CC(=O)N(O)C3=O)C3C(=CC=CC=3)[C:16]=2C=[CH:14][CH:13]=1.[CH3:34][CH2:35][O:36][CH2:37][CH3:38]>O.CC(C)=O>[CH3:34][CH2:35][O:36][CH2:37][CH3:38].[CH3:14][CH2:13][CH2:12][CH:24]([CH3:23])[CH3:16]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 10340Sodium Carbonate2×HCID 69111994HCID 69111994, compound

Product 1

HCID 21882825Ether isohexane

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

The deprotected imidazole derivative (3.9 g, 14 mmole) was dissolved in water (50 ml), acetone (30 ml) and 1M sodium carbonate (30 ml) and the solution was cooled in an ice bath. 9-Fluorenylmethyl-N-hydroxysuccinimide (4.76 g) in acetone (30 ml) was added dropwise with stirring over a period of 20 minutes (pH maintained at 9 by the addition of 1M sodium carbonate solution) and the stirring was continued overnight. Acetone was removed by evaporation and the aqueous solution was acidified with 1M KHSO4 and the product was extracted into ethyl acetate. The organic phase was washed with water and saturated sodium chloride solution, dried over MgSO4, and evaporated to leave an oil. Trituration with ether and ether/isohexane gave a solid [3.66 g, 66%; (M+H)+ 392].

Workup

  1. waitwas continued overnight
  2. customAcetone was removed by evaporation
  3. extractionthe product was extracted into ethyl acetate
  4. washThe organic phase was washed with water and saturated sodium chloride solution
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customto leave an oil

Sources & evidence

ORD record
ord-e7bf423096544233a0dc7e880bfc7adb
Source dataset
uspto-grants-2000_03
Patent number
US06034056

Reaction notes

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