p-Toluenesulfonyl azide → (E)-2-diazo-3-oxo-6-octenoic acid methyl ester

HRID 616292Notes

Reaction equation

HRID 616292 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5](=[O:11])[CH2:6][CH2:7]/[CH:8]=[CH:9]/[CH3:10].C1(C)C=CC(S([N:22]=[N+:23]=[N-])(=O)=O)=CC=1>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:12])[C:4](=[N+:22]=[N-:23])[C:5](=[O:11])[CH2:6][CH2:7]/[CH:8]=[CH:9]/[CH3:10]

Participants

4

Reactant 2

HCID 13661p-Toluenesulfonyl azideHCID 6278738Methyl 3-oxo-6-octenoate

Product 1

HCID 86735461(E)-2-diazo-3-oxo-6-octenoic acid methyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In accordance with the process of Example 2, (E)-3-oxo-6-octenoic acid methyl ester (3.42 g; 20.1 m mol), triethylamine (2.03 g; 20.1 m mol), p-toluenesulfonyl azide(3.99 g; 20 m mol) were used as starting materials to obtain 3.37 g of (E)-2-diazo-3-oxo-6-octenoic acid methyl ester as yellow oily product.

Sources & evidence

ORD record
ord-252e8c5500574a019909c4b7e9da2c9d
Source dataset
uspto-grants-1978_02
Patent number
US04073799

Reaction notes

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