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

HRID 839276Notes

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

Reactant 3

HCID 8471Triethylamine

HCID 13661p-Toluenesulfonyl azide

HCID 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%

Procedure

In accordance with the process of Preparation 1, 3-oxo-5-trimethylsilyloxy-6-heptenoic acid methyl ester (360 mg; 1.47 mmol), p-toluenesulfonyl azide (290 mg; 1.47 mmol) and triethylamine (150 mg; 1.47 mmol) were used as starting materials to obtain 330 mg of 2-diazo-3-oxo-5-trimethylsilyloxy-6-heptenoic acid methyl ester as a yellow oily product.

Sources & evidence

ORD record: ord-57881d6eff9848cbbcd41388ed57880c
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04094886

Reaction notes

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