Triethylamine → HCID 54201425, compound

HRID 1905003Notes

Reaction equation

HRID 1905003 reaction equation
[N+:1](=[C:3]([C:10](=[O:13])[CH2:11][CH3:12])[C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5])=[N-:2].C(N(CC)CC)C.O([Si](C)(C)C)S(C(F)(F)F)(=O)=O.[Br:33]Br>C(Cl)Cl>[N+:1](=[C:3]([C:10](=[O:13])[CH:11]([Br:33])[CH3:12])[C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5])=[N-:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24408BromineHCID 65367Trimethylsilyl triflateHCID 54468657HCID 54468657, compound

Product 1

HCID 54201425HCID 54201425, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled solution of allyl 2-diazo-3-ketopentanoate (9.1 g, 0.05 mole) in 100 mL of CH2CL2, was added 8.35 mL of triethylamine, followed by dropwise addition of 11.6 mL trimethylsilyl triflate (13.34 g, 0.06 mole) over twenty minutes. The resulting solution (orange) was stirred at 0° C. for one hour. A solution of bromine (8.0 g, 0.05 mole) in 30 mL CH2Cl2 was added over twenty minutes at 0° C. The mixture was stirred at 0° C. for one hour. The reaction mixture was then washed with water three times, dried over magnesium sulphate and concentrated to give the title compound as an oil (12.74 G, 97% yield).

Workup

  1. stirringThe mixture was stirred at 0° C. for one hour
  2. washThe reaction mixture was then washed with water three times
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-266acb3ee4c840548dc9022b61792d0f
Source dataset
uspto-grants-1989_06
Patent number
US04841043

Reaction notes

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