Triethylamine → 1,3-Cyclohexanedione, 2-diazo-5-phenyl-

HRID 127828

Reaction equation

HRID 127828 reaction equation
[C:1]1([CH:7]2[CH2:12][C:11](=[O:13])[CH2:10][C:9](=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.S([N:32]=[N+:33]=[N-])(C1C=CC(C)=CC=1)(=O)=O>C(O)C>[N+:32](=[C:10]1[C:9](=[O:14])[CH2:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12][C:11]1=[O:13])=[N-:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 5689621,3-Cyclohexanedione, 5-phenyl-

Product 1

HCID 108892501,3-Cyclohexanedione, 2-diazo-5-phenyl-Yield 36.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 20.0 g (0.106 mol) of 5-phenyl-cyclohexane-1, 3-dione in 75 ml ethanol was cooled to -10° C. and stirred magnetically under nitrogen. To the mixture was added 10.75 g (0.106 mol) of triethylamine. The tosyl azide (20.95 g 0.106 mol) was added all at once, and the mixture stirred for one hour at 0°-5° C. The solvent was removed under vacuum at a temperature less than 40° C. To the residue was added 200 ml ether, and the mixture extracted with a solution containing 3.1 g potassium hydroxide in 200 ml of water. The ethereal solution was dried over anhydrous MgSO4 filtered and the solvent removed to give a yellow solid which was recrystallized from ethanol-hexane to give 8.38 g (32%) of 2-diazo-5-phenyl-cyclohexane-1, 3-dione as yellow crystals, mp 122°-124° C.

Workup

  1. stirringstirred for one hour at 0°-5° C
  2. customThe solvent was removed under vacuum at a temperature less than 40° C
  3. additionTo the residue was added 200 ml ether
  4. extractionthe mixture extracted with a solution
  5. additioncontaining 3.1 g potassium hydroxide in 200 ml of water
  6. dry with materialThe ethereal solution was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. customthe solvent removed
  9. customto give a yellow solid which
  10. customwas recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-af3b91f662af4a14b9cdb2db6487acfd
Source dataset
uspto-grants-1981_03
Patent number
US04257858

Linked notes

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