3-Oxabicyclo[3.1.0]hexane-6-carboxylicacid,ethylester(9CI)

3-Oxabicyclo[3.1.0]hexane-6-carboxylicacid,ethylester(9CI) Property

storage temp. 

Sealed in dry,Room Temperature

Appearance

Colorless to light yellow Liquid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

warning

Hazard statements

H302Harmful if swallowed

H313May be harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

3-Oxabicyclo[3.1.0]hexane-6-carboxylicacid,ethylester(9CI) Chemical Properties,Usage,Production

Synthesis

The suspension was heated and stirred at 90-100 °C with 2,5-dihydrofuran (14 g, 200 mmol) and Cu(II)(acac)2 (1.05 g, 4 mmol). Subsequently, a benzene (PhH, 240 mL) solution of ethyl azidoacetate (27.3 g, 240 mmol) was slowly added dropwise to the reaction system over a period of 3 hours. After completion of the dropwise addition, the reaction mixture was cooled to room temperature and the solvent was removed by evaporation. The residue was dissolved in petroleum ether and purified by adsorption through a neutral alumina column (240 g of alumina per 10 mmol of diazoxide), eluting sequentially with 500 mL of petroleum ether and 500 mL of ether (Et2O). Removal of the solvent from the eluent gave the crude product ester, which was subjected to reduced pressure distillation at about 105°C (18-19 mmHg). The fractions were further purified by silica gel (SiO2) column chromatography using gradient elution with ethyl acetate (EtOAc)/hexane (0 to 30% EtOAc), resulting in 15.39 g (45.8% yield) of ethyl 3-oxo-bicyclo[3.1.0]hexane-6-carboxylate as the target product (Ref: I. Reichelt and H. J. Reissig , Chem. Ber. 1983, 116, 3895).

References

[1] Patent: US2008/249087, 2008, A1. Location in patent: Page/Page column 26-27