p-Toluenesulfonyl azide → 2-Diazonio-1-methoxy-3-oxo-5-[(trimethylsilyl)oxy]hepta-1,6-dien-1-olate

HRID 616295Notes

Reaction equation

HRID 616295 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5](=[O:15])[CH2:6][CH:7]([O:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH2:9].C1(C)C=CC(S([N:26]=[N+:27]=[N-])(=O)=O)=CC=1>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:16])[C:4](=[N+:26]=[N-:27])[C:5](=[O:15])[CH2:6][CH:7]([O:10][Si:11]([CH3:13])([CH3:14])[CH3:12])[CH:8]=[CH2:9]

Participants

4

Reactant 2

HCID 13661p-Toluenesulfonyl azideHCID 53718342Methyl 3-oxo-5-[(trimethylsilyl)oxy]hept-6-enoate

Product 1

HCID 539183532-Diazonio-1-methoxy-3-oxo-5-[(trimethylsilyl)oxy]hepta-1,6-dien-1-olateYield 83%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In accordance with the process of Example 2, 3-oxo-5-trimethylsilyloxy-6-heptenoic acid methyl ester (360 mg; 1.47 m mol), p-toluenesulfonyl azide(290 mg; 1.47 m mol) and triethylamine (150 mg; 147 m mol) were used as starting materials to obtain 330 mg of 2-diazo-3-oxo-5-trimethylsiloxy-6-heptenoic acid methyl ester as yellow oily product.

Sources & evidence

ORD record
ord-0ae91c5a8d7c43e8819c22356b465a44
Source dataset
uspto-grants-1978_02
Patent number
US04073799

Reaction notes

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