ethyl 1-acetylcyclopropanecarboxylate Chemical Properties

Boiling point:

42-44 °C(Press: 2 Torr)

Density 

1.139±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C8H12O3/c1-3-11-7(10)8(4-5-8)6(2)9/h3-5H2,1-2H3

InChIKey

DISZFIFAESWGBI-UHFFFAOYSA-N

SMILES

C1(C(C)=O)(C(OCC)=O)CC1

Safety Information

WGK Germany 

WGK 3

HS Code 

2902190000

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2

ethyl 1-acetylcyclopropanecarboxylate Usage And Synthesis

Uses

ethyl 1-methyl cyclopropanecarboxylate is an important pharmaceutical intermediate used in the addition of cyclopropane.

Synthesis

Step 1) Synthesis of ethyl 1-acetylcyclopropanecarboxylate: To a solution of ethyl 3-oxobutanoate (26 g, 200 mmol) in acetone (500 mL) was added potassium carbonate (82.8 g, 600 mmol) followed by 1,2-dibromoethane (45.12 g, 240 mmol). The reaction mixture was refluxed for 24 hours. After completion of the reaction, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography with an eluent ratio of 1:50 (v/v) ethyl acetate/hexane to afford the target compound ethyl 1-acetylcyclopropanecarboxylate as a colorless oil (18.7 g, 60% yield). Mass spectrum (ESI, cation mode) m/z: 157 (M+1); 1H NMR (400 MHz, CDCl3) δ: 1.25-1.29 (t, J=7.2 Hz, 3H), 1.45 (s, 4H), 2.45 (s, 3H), 4.18-4.20 (q, 2H).

References

[1] Tetrahedron Letters, 2005, vol. 46, # 4, p. 635 - 638
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 2, p. 420 - 422
[3] Tetrahedron Asymmetry, 2010, vol. 21, # 5, p. 631 - 635
[4] Journal of Organic Chemistry, 2011, vol. 76, # 8, p. 2807 - 2813
[5] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, vol. 19, # 6, p. 644 - 650