Dimethyl Sulfoxide → Beta-naphthyl ketone

HRID 1664098Notes

Reaction equation

HRID 1664098 reaction equation
[N-]=[N+]=[N-].[Na+].[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[C:15]([C:17](Br)([CH3:19])[CH3:18])=[O:16].CS(C)=O>O>[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[C:15]([C:17]1[CH:19]=[CH:15][C:6]2[C:5](=[CH:14][CH:9]=[CH:8][CH:7]=2)[CH:18]=1)=[O:16]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 33557Sodium AzideHCID 12587407alpha-Bromoisopropyl 2-naphthyl ketone

Product 1

HCID 10945915Beta-naphthyl ketoneYield 146.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.75 g of sodium azide was added to a mixture comprising 1.59 g of α-bromoisopropyl 2-naphthyl ketone and 40 ml of dimethyl sulfoxide, and the mixture was reacted at 50° C. for 1.5 hours. The reaction mixture was put into water and extracted with ethyl acetate, followed by washing with water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/9) to obtain 1.19 g of oily α-azideisopropyl 2-naphthyl ketone.

Workup

  1. customthe mixture was reacted at 50° C. for 1.5 hours
  2. extractionextracted with ethyl acetate
  3. washby washing with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/9)

Sources & evidence

ORD record
ord-920a9465e4d6450b90bffdad950ec108
Source dataset
uspto-grants-2011_10
Patent number
US08039420B2

Reaction notes

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