1,2-Dibromoethane → tert-Butyl 1-acetylcyclopropanecarboxylate

HRID 2283421Notes

Reaction equation

HRID 2283421 reaction equation
[C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].Br[CH2:13][CH2:14]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CCOCC>[C:3]([C:2]1([C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:14][CH2:13]1)(=[O:4])[CH3:5]

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 15538Tert-butyl acetoacetate

Product 1

HCID 57434365tert-Butyl 1-acetylcyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
55 °C

Procedure

Step 1 A stirred suspension of tert-butyl acetoacetate (2.1 mL, 12.6 mmol), 1,2-dibromoethane (1.14 mL, 13.3 mmol) and potassium carbonate (3.49 g, 25.3 mmol) in acetone (50.6 mL) was heated to 55° C. over a weekend. Upon cooling the mixture was diluted with Et2O and washed with water (×2). The organic phase was dried (Na2SO4), filtered and concentrated. Biotage column (40+M) eluting with a gradient of 0% Et2O/petrol to 20% Et2O/petrol gave tert-butyl 1-acetylcyclopropane-1-carboxylate, 0.78 g, 29%. 1H NMR (400 MHz, CDCl3): 2.46 (3H, s), 1.51 (9H, s), 1.43-1.38 (4H, m).

Workup

  1. temperatureUpon cooling the mixture
  2. washwashed with water (×2)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washBiotage column (40+M) eluting with a gradient of 0% Et2O/petrol to 20% Et2O/petrol

Sources & evidence

ORD record
ord-ff70b11dff2649d4a74de1ae034beec9
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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