Tributylphosphine → HCID 178472854, compound

HRID 449960Notes

Reaction equation

HRID 449960 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-8edec27eeefa43878a000b3927fbc4ef
Source dataset
uspto-grants-2013_07
Patent number
US08486946B2

Reaction notes

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