Cyclobutanecarboxylic acid → HCID 15444481, compound

HRID 1475629Notes

Reaction equation

HRID 1475629 reaction equation
[CH:1]1([C:5]([OH:7])=[O:6])[CH2:4][CH2:3][CH2:2]1.ClC(Cl)(Cl)C(=N)O[C:12]([CH3:15])([CH3:14])[CH3:13].C(=O)(O)[O-].[Na+]>C1COCC1>[CH:1]1([C:5]([O:7][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 19494Cyclobutanecarboxylic acidHCID 516892Sodium BicarbonateHCID 2734700Tert-butyl 2,2,2-trichloroethanimidate

Product 1

HCID 15444481HCID 15444481, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 99 μl (0.78 mmol) of boron trifluoride/diethyl ether complex were added to 5.2 g (52.3 mmol) of cyclobutanecarboxylic acid in 100 ml of THF. A little at a time, 13.7 g (62.75 mmol) of tert-butyl 2,2,2-trichloroethaneimidoate were then added, and the mixture was subsequently stirred at room temperature overnight. 5 g of sodium bicarbonate were then added, and the reaction mixture was stirred for 15 min. After filtration, the solution was concentrated to dryness under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 4:1). This gave 5.2 g (64% of theory) of the title compound as a yellow oil.

Workup

  1. stirringthe reaction mixture was stirred for 15 min
  2. filtrationAfter filtration
  3. concentrationthe solution was concentrated to dryness under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-55839f5bf4f443adb79ead6aaac2a26c
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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