Triethylamine → 2-Diazonio-1-methoxy-3-oxohepta-1,6-dien-1-olate

HRID 839271Notes

Reaction equation

HRID 839271 reaction equation
C1(C)C=CC(S([N:10]=[N+:11]=[N-])(=O)=O)=CC=1.[CH3:14][O:15][C:16](=[O:24])[CH2:17][C:18](=[O:23])[CH2:19][CH2:20][CH:21]=[CH2:22].C(N(CC)CC)C>C(#N)C>[CH3:14][O:15][C:16](=[O:24])[C:17](=[N+:10]=[N-:11])[C:18](=[O:23])[CH2:19][CH2:20][CH:21]=[CH2:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 366065Methyl 3-oxo-6-heptenoate

Product 1

HCID 540756342-Diazonio-1-methoxy-3-oxohepta-1,6-dien-1-olateYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of p-toluenesulfonyl azide (592 mg; 3 mmol) in 1 ml of acetonitrile was added at room temperature to a solution of 3-oxo-6-heptenoic acid methyl ester (468 mg; 3 mmol) and triethylamine (306 mg; 3 mmol) in 5 ml of acetonitrile. The mixture was stirred for about 2 hours and the solvent was distilled off under a reduced pressure and the product was dissolved in 50 ml of ether. The solution was washed with a 5% aqueous solution of potassium hydroxide until no color remained in the aqueous phase and was further washed with a saturated aqueous solution of sodium chloride. The ether solution was dried over anhydrous magnesium sulfate and was filtered and condensed under a reduced pressure to obtain 530 mg of 2-diazo-3-oxo-6-heptenoic acid methyl ester as a yellow oily product. The crude product can be purified by distillation under reduced pressure.

Workup

  1. distillationthe solvent was distilled off under a reduced pressure
  2. dissolutionthe product was dissolved in 50 ml of ether
  3. washThe solution was washed with a 5% aqueous solution of potassium hydroxide until no color
  4. washwas further washed with a saturated aqueous solution of sodium chloride
  5. dry with materialThe ether solution was dried over anhydrous magnesium sulfate
  6. filtrationwas filtered
  7. customcondensed under a reduced pressure

Sources & evidence

ORD record
ord-7d2deaeffdb7406c994a28be90ca526a
Source dataset
uspto-grants-1978_06
Patent number
US04094886

Reaction notes

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