Ethyl 2-oxovalerate

Ethyl 2-oxovalerate Property

Boiling point:

182.5°C (estimate)

Density 

0.9985

refractive index 

1.4170

storage temp. 

2-8°C

solubility 

Chloroform, DMSO, Methanol

form 

Oil

color 

Pale yellow

InChI

InChI=1S/C7H12O3/c1-3-5-6(8)7(9)10-4-2/h3-5H2,1-2H3

InChIKey

YERWBBMSDMSDKT-UHFFFAOYSA-N

SMILES

C(OCC)(=O)C(=O)CCC

CAS DataBase Reference

50461-74-0(CAS DataBase Reference)

Safety

HS Code 

2918300090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H290May be corrosive to metals

H314Causes severe skin burns and eye damage

H341Suspected of causing genetic defects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P234Keep only in original container.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P308+P313IF exposed or concerned: Get medical advice/attention.

P363Wash contaminated clothing before reuse.

P390Absorb spillage to prevent material damage.

P405Store locked up.

P406Store in corrosive resistant/… container with a resistant inner liner.

P501Dispose of contents/container to..…

Ethyl 2-oxovalerate Chemical Properties,Usage,Production

Chemical Properties

Light yellow oil liquid

Uses

Ethyl 2-oxopentanoate is used as a reagent to synthesize selective CB1 cannabinoid receptor antagonists. Ethyl 2-oxopentanoate is also used to synthesize derivatives of iminodiacid, an inhibitor of angiotensin converting enzyme.

Synthesis

General procedure: 0.1 mole of 2,2-(dimethylthio)pentanoic acid (19.4 g) was dissolved in 150 mL of toluene, 2.0 equivalents of H2O (3.6 mL) and a trace amount of p-toluenesulfonic acid monohydrate were added. The mixture was heated to boiling point and a stream of nitrogen was passed through the glass feed. After refluxing for 3 hours and cooling to 80°C, 200 mL of ethanol and trace amounts of p-toluenesulfonic acid monohydrate were added. Reflow was continued for 3 hours, cooled to 20°C, 200 ml of water was added and extracted three times with diethyl ether (100 ml each time). The ether phases were combined, washed to neutrality with dilute sodium bicarbonate solution and dried over magnesium sulfate. After filtration, the solvent was removed by rotary evaporation to give ethyl 2-oxovalerate (10.2 g, 71% yield) as a light yellow oil.1H NMR (500 MHz, CDCl3): δ=0.97 (t, J=7.3 Hz, 3H), 1.37 (t, J=7.3 Hz, 3H), 1.67 (sext, J=7.3 Hz, 2H). 2.81 (t, J=7.3Hz, 2H), 4.32 (q, J=7.3Hz, 2H).13C NMR (125.8MHz, CDCl3): δ=13.5, 14.0, 16.6, 41.2, 62.3, 161.4, 194.7.

References

[1] Patent: US2009/76302, 2009, A1. Location in patent: Page/Page column 7