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

HRID 839275Notes

Reaction equation

HRID 839275 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5](=[O:18])[CH:6]=[C:7]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:8][CH3:9].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 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 57132993HCID 57132993, compound

Product 1

HCID 540398955-(Benzyloxy)-2-diazonio-1-methoxy-3-oxohepta-1,6-dien-1-olateYield 98.1%

Procedure

In accordance with the process of Preparation 1, 5-benzyloxy-3-oxo-heptenoic acid methyl ester (1.07 g; 4.1 mmol), p-toluene-sulfonyl azide (810 mg; 4.1 mmol) and triethylamine (450 mg; 4.5 mmol) were used as starting materials to obtain 1.16 g of 5-benzyloxy-2-diazo-3-oxo-6-heptenoic acid methyl ester as a yellow oily product.

Sources & evidence

ORD record
ord-fd4cb30f7a804aabbe1e14a1d8d3bfb6
Source dataset
uspto-grants-1978_06
Patent number
US04094886

Reaction notes

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