Benzenediazonium tetrafluoroborate → Methyl 2-phenyl-2-phenylhydrazonoacetate

HRID 622819

Reaction equation

HRID 622819 reaction equation
[CH3:1][O:2][C:3]([O:11][Si](C)(C)C)=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.F[B-](F)(F)F.[C:21]1([N+:27]#[N:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1C=CC=CC=1.C(OCC)C>[C:5]1([C:4](=[N:28][NH:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:3]([O:2][CH3:1])=[O:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 5284485Benzenediazonium tetrafluoroborateHCID 54141957(1-Methoxy-2-phenylvinyloxy)trimethylsilane

Product 1

HCID 21812006Methyl 2-phenyl-2-phenylhydrazonoacetateYield 84%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

1.0 mmol of (1-methoxy-2-phenylethenyl)oxytrimethylsilane was placed in a 20-ml flask, followed by the addition of 3 ml of pyridine as a solvent. 1.3 mmol of benzenediazonium tetrafluoroborate was added to the flask. The obtained mixture was stirred at 0° C. in a nitrogen atmosphere for 2 hours. The reaction mixture was diluted with diethyl ether and washed with 1.5N hydrochloric acid, water and a saturated aqueous solution of common salt successively. The obtained organic phase was dried over magnesium sulfate and distilled under a reduced pressure to remove the solvent. The obtained oily mixture was subjected to silica gel thin-layer chromatography to obtain 0.84 mmol of methyl 2-phenyl-2-phenylhydrazonoacetate.

Workup

  1. washwashed with 1.5N hydrochloric acid, water
  2. dry with materialThe obtained organic phase was dried over magnesium sulfate
  3. distillationdistilled under a reduced pressure
  4. customto remove the solvent

Sources & evidence

ORD record
ord-6b70e06a7da644bdaaae099a34744b65
Source dataset
uspto-grants-1988_09
Patent number
US04772714

Linked notes

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