Trifluoroacetic acid → HCID 89869762, compound

HRID 571620Notes

Reaction equation

HRID 571620 reaction equation
C(OC([N:8]([CH2:16][CH:17]=[CH2:18])/[N:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:16]([NH:8]/[N:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:17]=[CH2:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89867118HCID 89867118, compound

Product 1

HCID 89869762HCID 89869762, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of E-ethyl 2-(2-t-butoxycarbonyl-2-allylhydrazono)acetate (8.65 g, 33.7 mmol) in dichloromethane (60 ml) was added trifluoroacetic acid (15 ml) at 3° C. After being stirred at room temperature for 1 hour, concentrated in vacuo. The residue was added to a saturated aqueous sodium hydrogen carbonate solution (300 ml), and extracted with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 1.87 g of E-ethyl 2-(2-allylhydrazono)acetate (yield 35%) as oil.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was added to a saturated aqueous sodium hydrogen carbonate solution (300 ml)
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-79c3a80a9eff4901b4130113da39db61
Source dataset
uspto-grants-2015_05
Patent number
US09029295B2

Reaction notes

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