Tributylphosphine → HCID 178472857, compound

HRID 2067123Notes

Reaction equation

HRID 2067123 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](=[O:16])[C:8](=[N+:14]=[N-:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10].C(P(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](=[O:16])/[C:8](=[N:14]/[NH2:15])/[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 516892Sodium BicarbonateHCID 86662102HCID 86662102, compound

Product 1

HCID 178472857HCID 178472857, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 3-(3-chloro-2-thienyl)-2-diazo-3-oxopropanoate (662 mg, 2.56 mmol) was dissolved in dioxane (10 mL), treated with tri-n-butylphosphine (0.663 mL, 2.69 mmol, 1.05 equiv) and stirred at ambient temperature for 30 minutes. The mixture was poured into sodium bicarbonate (100 mL, aqueous saturated) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 1:1; hexanes:ethyl acetate), providing the titled compound.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel gradient chromatography (100:0 to 1:1; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-601e5204adc6438691679eac9adec9f9
Source dataset
uspto-grants-2012_10
Patent number
US08293744B2

Reaction notes

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