p-Toluenesulfonyl azide → 5-(Benzyloxy)-2-diazonio-1-methoxy-3-oxohepta-1,6-dien-1-olate

HRID 616294Notes

Reaction equation

HRID 616294 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5](=[O:18])[CH2:6][CH:7]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:8]=[CH2:9].C1(C)C=CC(S([N:29]=[N+:30]=[N-])(=O)=O)=CC=1>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:19])[C:4](=[N+:29]=[N-:30])[C:5](=[O:18])[CH2:6][CH:7]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:8]=[CH2:9]

Participants

4

Reactant 2

HCID 13661p-Toluenesulfonyl azideHCID 54138168Methyl 5-(benzyloxy)-3-oxohept-6-enoate

Product 1

HCID 540398955-(Benzyloxy)-2-diazonio-1-methoxy-3-oxohepta-1,6-dien-1-olateYield 98.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In accordance with the process of Example 2, 5-benzyloxy-3-oxo-6-heptenoic acid methyl ester (1.07 g; 4.1 m mol), p-toluenesulfonyl azide (810 mg; 4.1 m mol) and triethylamine (450 mg; 4.5 m mol) were used as starting materials to obtain 1.16 g of 5-benzyloxy-2-diazo-3-oxo-6-heptenoic acid methyl ester as yellow oily product.

Sources & evidence

ORD record
ord-e921307e485947c2a21e6fa3b60e9b21
Source dataset
uspto-grants-1978_02
Patent number
US04073799

Reaction notes

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