Tributylphosphine → ethyl 3-(3-chloro-2-fluorophenyl)-2-hydrazinylidene-3-oxopropanoate

HRID 449971

Reaction equation

HRID 449971 reaction equation
[Cl:1][C:2]1[C:3]([F:18])=[C:4]([C:8](=[O:17])[C:9](=[N+:15]=[N-:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1.C(P(CCCC)CCCC)CCC>O1CCOCC1>[CH2:13]([O:12][C:10](=[O:11])[C:9](=[N:15][NH2:16])[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[F:18])=[O:17])[CH3:14]

Participants

4

Reactant 2

HCID 13831TributylphosphineHCID 86659989Ethyl 3-(3-chloro-2-fluorophenyl)-2-diazo-3-oxopropanoate

Product 1

HCID 178472855ethyl 3-(3-chloro-2-fluorophenyl)-2-hydrazinylidene-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 3-(3-chloro-2-fluorophenyl)-2-diazo-3-oxopropanoate (1.28 g, 4.73 mmol) in dioxane (12 mL) was added tri-n-butylphosphine (1.23 mL, 4.97 mmol). After stirring for 10 minutes at ambient temperature, the mixture was concentrated in vacuo and the residue was purified by silica gel gradient chromatography (100:0 to 40:60 hexane:ethyl acetate), providing the titled compound.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue was purified by silica gel gradient chromatography (100:0 to 40:60 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-c615c68c0dfe420da488f33131fc639b
Source dataset
uspto-grants-2013_07
Patent number
US08486946B2

Linked notes

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