1-[3-(2-Methyl-1,3-dioxolan-2-yl)propyl]-1H-imidazole → 5-(1H-Imidazol-1-yl)pentan-2-one

HRID 1583426Notes

Reaction equation

HRID 1583426 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)OCC[O:3]1>Cl>[N:10]1([CH2:9][CH2:8][CH2:7][C:2](=[O:3])[CH3:1])[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

3

Reactant 1

HCID 135575621-[3-(2-Methyl-1,3-dioxolan-2-yl)propyl]-1H-imidazole

Product 1

HCID 125919545-(1H-Imidazol-1-yl)pentan-2-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 48.4 g of 1-[3-(2-methyl-1,3-dioxolan-2-yl)-propyl]-1H-imidazole in 615 ml of 1M hydrochloric acid was stirred overnight. The reaction mixture was concentrated to half volume under reduced pressure and the solution was made basic with sodium hydroxide and extracted with dichloromethane. The combined organic layers were dried over potassium carbonate and the residue obtained after concentration was distilled to yield 30.17 g (77%), bp 110°-121° C./0.1 min. A sample was further purified on silica gel thick layer plates eluting with 9% methanol-dichloromethane to give an analytical sample of 5-(1H-imidazol-1-yl)-2-pentanone.

Workup

  1. concentrationThe reaction mixture was concentrated to half volume under reduced pressure
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over potassium carbonate
  4. customthe residue obtained
  5. concentrationafter concentration
  6. distillationwas distilled
  7. customto yield 30.17 g (77%), bp 110°-121° C./0.1 min
  8. customA sample was further purified on silica gel thick layer plates
  9. washeluting with 9% methanol-dichloromethane

Sources & evidence

ORD record
ord-e3d6612d209d4323bf2a911b95946d0e
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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