ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate Chemical Properties

Boiling point:

293.0±40.0 °C(Predicted)

Density 

1.12±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Dichloromethane, Ethyl Acetate

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C11H18O4/c1-2-13-10(12)9-3-5-11(6-4-9)14-7-8-15-11/h9H,2-8H2,1H3

InChIKey

UXXWGBLTOSRBAY-UHFFFAOYSA-N

SMILES

O1C2(CCC(C(OCC)=O)CC2)OCC1

ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate Usage And Synthesis

Uses

ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate can be used in the preparation of arylcyclohexanones analgesics, metalloproteinase inhibitors, benzimidazole derivatives as therapeutic TRPM8 receptor modulators and aposptosis inducing agents.

Synthesis

Ethyl 4-oxo-cyclohexanecarboxylate (52.8 g, 0.31 mol), ethylene glycol (67.4 g, 1.08 mol) and p-toluenesulfonic acid (0.7 g) were dissolved in toluene (160 mL) and the reaction mixture was stirred at room temperature. After the reaction was completed, the reaction solution was poured into ether (300 mL), washed sequentially with water, sodium bicarbonate solution and sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a colorless liquid product. The product was directly used in the next reaction without further purification, yield: 66.5 g (100%).1H-NMR (CDCl3) δ: 1.24 (t, 3H), 1.53 (m, 2H), 1.76 (m, 4H), 1.92 (m, 2H), 2.31 (m, 1H), 3.91 (s, 4H), 4.11 (q, 2H).13C- NMR (CDCl3) δ: 14.28 (q), 26.32 (t), 33.76 (t), 41.59 (d), 60.14 (t), 64.21 (t), 107.90 (d), 174.77 (s). Sec-butanediol (1.08 mol) and p-toluenesulfonic acid (0.7 g) were added to a solution of ethyl 4-oxo-cyclohexanecarboxylate (0.31 mol) in toluene (160 mL) and stirred for 20 hr at 25 °C. At the end of the reaction, ethyl acetate (300 mL) was added, and the organic phase was separated, washed sequentially with water, saturated aqueous sodium bicarbonate solution, and sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure. The resulting product can be used in the next reaction without further purification.

References

[1] Synthesis, 1998, # 4, p. 436 - 443
[2] Patent: US2008/306084, 2008, A1. Location in patent: Page/Page column 33-34; 44-45
[3] Patent: US2008/312231, 2008, A1. Location in patent: Page/Page column 17
[4] Patent: US2009/48323, 2009, A1. Location in patent: Page/Page column 14; 16
[5] Patent: US2009/111842, 2009, A1. Location in patent: Page/Page column 8

ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate(1489-97-0)Related Product Information

• (1,4-DIOXA-SPIRO[4.5]DEC-8-YL)-ACETIC ACID ETHYL ESTER