2-(2-Bromoethoxy)tetrahydro-2H-pyran

Chemical Properties

Clear pale yellow liquid

Uses

2-(2-Bromoethoxy)tetrahydro-2H-pyran may be used in the synthesis of:

• 4-(2-chloroethoxy)benzenesulfonyl chloride
• estrogen ligands bearing carborane
• 2-(2-(1,3-di((E)-2-(2-(2-(2-(5-(4-(tert-butoxycarbonyl(methyl)amino)styryl)pyridin-2-yloxy)ethoxy)ethoxy)ethoxy)ethoxy)propan-2-yloxy)ethoxy)-tetrahydro-2H-pyran

General Description

2-(2-Bromoethoxy)tetrahydro-2H-pyran is an organic building block. It has been synthesized by employing 2-bromoethanol as a starting reagent.

Synthesis

To a mixed solution of 2-bromoethanol (3.8 g, 30.0 mmol) and 3,4-dihydro-2H-pyran (2.5 g, 30.0 mmol) dissolved in dichloromethane (50 mL), p-toluenesulfonic acid (380.0 mg, 2.2 mmol) was added in portions. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the mixture was concentrated and purified by silica gel column chromatography (petroleum ether/ethyl acetate, 50:1) to afford 2-(2-bromoethoxy)tetrahydro-2H-pyran (5.6 g, yield: 89%) as a colorless oil.

References

[1] Collection of Czechoslovak Chemical Communications, 2004, vol. 69, # 10, p. 1843 - 1876
[2] Chinese Chemical Letters, 2010, vol. 21, # 10, p. 1165 - 1166
[3] Phosphorus, Sulfur and Silicon and Related Elements, 1998, vol. 132, p. 219 - 229
[4] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 350, p. 51 - 65
[5] Patent: WO2008/76949, 2008, A2. Location in patent: Page/Page column 28