Ethyl phenylacetate → 2-Diazonio-1-ethoxy-2-phenylethen-1-olate

HRID 2404431Notes

Reaction equation

[C:1]1([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S([N:22]=[N+:23]=[N-])(=O)=O)=CC=1.N12CCCN=C1CCCCC2>C(#N)C>[CH2:11]([O:10][C:8](=[O:9])[C:7](=[N+:22]=[N-:23])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl phenylacetate (3.28 g) in acetonitrile (60 mL) is added para-toluenesulfonylazide (4.53 g). The reaction mixture is cooled to 0° C. and 1,8-diazabicyclo[5.4.0]undec-7-ene (3.9 mL) is added dropwise. The reaction mixture is kept at 5° C. overnight. Solvent is removed to dryness and the residue is purified by chromatography (gradient petroleum ether/dichloromethane from 90/10 to 80/20) to give diazophenylacetic acid ethyl ester;

Workup

customSolvent is removed to dryness
customthe residue is purified by chromatography (gradient petroleum ether/dichloromethane from 90/10 to 80/20)

Sources & evidence

ORD record: ord-ebf8af25f446471b9d30118200951f04
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802664B2

Reaction notes

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