Ethyl diazoacetate → HCID 86732070, compound

HRID 1486757Notes

Reaction equation

HRID 1486757 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH2:9])[N:5]=[C:4]([CH3:10])[N:3]=1.[N+](=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N-]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([CH3:10])[N:5]=[C:6]([CH:8]2[CH2:9][CH:13]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=1

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 86732069HCID 86732069, compound

Product 1

HCID 86732070HCID 86732070, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 6-2 (15.0 g, 97 mmol) in toluene (300 mL) heating at 100° C. under a nitrogen atmosphere was added a solution of ethyl diazoacetate (30.2 mL, 291 mmol) in toluene (100 mL) over 1.5 h. Heating was continued for 2 h after which the reaction mixture was cooled to room temperature and concentrated to dryness. The residue was partitioned between saturated sodium bicarbonate solution (1 L) and ethyl acetate (1 L). The organic layer was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (0-100% EtOAc/hexanes) to give 6-3 (trans isomer) as a colorless oil. MS: m/z=241.1 (M+H).

Workup

  1. temperatureHeating
  2. concentrationconcentrated to dryness
  3. customThe residue was partitioned between saturated sodium bicarbonate solution (1 L) and ethyl acetate (1 L)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified by silica gel chromatography (0-100% EtOAc/hexanes)
  9. customto give 6-3 (trans isomer) as a colorless oil

Sources & evidence

ORD record
ord-7fb8a08185534aff921f8a9cee376130
Source dataset
uspto-grants-2016_08
Patent number
US09428492B2

Reaction notes

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