Tributylphosphine → HCID 178472854, compound

HRID 241996Notes

Reaction equation

HRID 241996 reaction equation
[N+:1](=[C:3]([C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-:2].C(P(CCCC)CCCC)CCC>C(#N)C>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9](=[O:10])[C:3](=[N:1][NH2:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 13831TributylphosphineHCID 76818128Ethyl 2-diazo-3-(2-fluorophenyl)-3-oxopropanoate

Product 1

HCID 178472854HCID 178472854, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-diazo-3-(2-fluorophenyl)-3-oxopropanoate (1.06 g, 4.49 mmol) was dissolved in acetonitrile (20 mL), cooled to 0° C. and treated with tri-n-butylphosphine (1.16 mL, 4.71 mmol, 1.05 equiv). The mixture was warmed to ambient temperature and after 10 minutes, was concentrated in vacuo. The residue was purified via silica gel gradient chromatography (100:0 to 75:25; hexanes:ethyl acetate) to provide the titled compound.

Workup

  1. temperatureThe mixture was warmed to ambient temperature and after 10 minutes
  2. concentrationwas concentrated in vacuo
  3. customThe residue was purified via silica gel gradient chromatography (100:0 to 75:25; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-3ac431d210894897a8f00f45dd932a68
Source dataset
uspto-grants-2014_02
Patent number
US08653079B2

Reaction notes

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