Imidazole → HCID 18467051, compound

HRID 2229251Notes

Reaction equation

HRID 2229251 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)=[O:6].C(N(CC)CC)C.CS(Cl)(=O)=O.[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>C1COCC1.[Na+].[I-].O>[N:29]1([CH2:2][CH2:3][CH2:4][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[O:6])[CH:33]=[CH:32][N:31]=[CH:30]1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 184670444-Hydroxy-1-(2-naphthyl)-1-butanone

Product 1

HCID 18467051HCID 18467051, compoundYield 22.7%

Reagents, catalysts & solvents 3

HCID 5238Sodium IodideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 4-hydroxy-1-(2-naphthyl)-1-butanone (4.32 g) in THF (60 ml) were added triethylamine (5.6 ml) and methanesulfonyl chloride (2.4 ml) successively. The mixture was stirred at 0° for 1 hour. Imidazole (2.93 g) and NaI (0.02 g) were added to the mixture and resulting mixture was refluxed for 16 hours. Water was added and the mixture was concentrated. The residue was extracted with ethyl acetate and the extract was washed with water and brine, dried and concentrated. The residue was chromatographed on silica gel, eluting with ethyl acetate-methanol=20:1, followed by crystallization from ethyl acetate-CH2Cl2-cyclohexane to give the titled compound (1.21 g) as a colorless solid.

Workup

  1. customresulting mixture
  2. temperaturewas refluxed for 16 hours
  3. concentrationthe mixture was concentrated
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe extract was washed with water and brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel
  9. washeluting with ethyl acetate-methanol=20:1
  10. customfollowed by crystallization from ethyl acetate-CH2Cl2-cyclohexane

Sources & evidence

ORD record
ord-8de3ba9fd7164ab49ee731895bf7df1e
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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