5-(Benzyloxy)-2-diazonio-1-methoxy-3-oxohepta-1,6-dien-1-olate → HCID 53869755, compound

HRID 839277Notes

Reaction equation

HRID 839277 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4](=[N+]=[N-])[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(C)=CC=CC=1>[CH3:1][O:2][C:3]([C:4]12[CH2:9][CH:8]1[CH:7]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:5]2=[O:18])=[O:21]

Participants

3

Reactant 1

HCID 540398955-(Benzyloxy)-2-diazonio-1-methoxy-3-oxohepta-1,6-dien-1-olate

Product 1

HCID 53869755HCID 53869755, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In accordance with the process of Preparation 22, 5-benzyloxy-2-diazo-3-oxo-6-heptenoic acid methyl ester (1.16 g; 4 mmol) and copper acetylacetone complex (100 mg) were dissolved in 30 ml of anhydrous xylene. The reaction product was purified by silica gel column chromatography to obtain two types of isomers of 4-benzyloxy-2-oxo-bicyclo[3.1.0] hexane-1-carboxylic acid methyl ester (248mg) as an oily product.

Workup

  1. customThe reaction product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ba22bac3efe54a6bb169f74dee7473b0
Source dataset
uspto-grants-1978_06
Patent number
US04094886

Reaction notes

Loading…