p-Toluenesulfonyl azide → 2-Diazonio-1-methoxy-7-methyl-3-oxoocta-1,6-dien-1-olate

HRID 616293Notes

Reaction equation

HRID 616293 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5](=[O:12])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10].C1(C)C=CC(S([N:23]=[N+:24]=[N-])(=O)=O)=CC=1>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:13])[C:4](=[N+:23]=[N-:24])[C:5](=[O:12])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 13661p-Toluenesulfonyl azideHCID 109102166-Octenoic acid, 7-methyl-3-oxo-, methyl ester

Product 1

HCID 538540242-Diazonio-1-methoxy-7-methyl-3-oxoocta-1,6-dien-1-olateYield 90%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In accordance with the process of Example 1, 3-oxo-7-methyl-6-octenoic acid methyl ester (0.54 g; 2.93 m mol), triethylamine (0.30 g; 2.93 m mol) and p-toluenesulfonyl azide (0.61 g; 2.93 m mol) were used as starting materials to obtain 0.55 g of 2-diazo-3-oxo-7-methyl-6-octenoic acid methyl ester as yellow oily product.

Sources & evidence

ORD record
ord-a9b9676530314a64988a3999275bda79
Source dataset
uspto-grants-1978_02
Patent number
US04073799

Reaction notes

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