Tetrahydrofuran → HCID 178436438, Verbindung

In a 100 mL flame-dried three-necked flask, fitted with refluxing condenser and dropping funnel, magnesium (92 mg, 3.82 mmol), iodine (1 mg) and dry THF (6 mL) were placed under nitrogen. A light brown solution formed, the mixture was heated to reflux, and a solution of 3-bromophenoxydimethylsilane (0.899 g, 3.47 mmol) in THF (20 mL) was added by dropping funnel over 2 hr. The reaction mixture was refluxed overnight and cooled to room temperature. Ethyldimethylchlorosilane (0.681 g, 0.78 mL, 5.55 mmol) was then added by syringe. The reaction mixture was brought to reflux again for 6 hr, and allowed to stir overnight at room temperature. The reaction was then quenched with 1N HCl, and the reaction concentrated in vacuo. Extraction with CH2Cl2, aqueous workup, and column chromatography (n-hexane/ethyl acetate 8:1) yielded 3-ethyldimethylsilyl phenol (0.130 g, 0.73 mmol, 21%) as a colorless oil.

1. customIn a 100 mL flame-dried three-necked flask, fitted
2. temperaturewith refluxing condenser
3. customA light brown solution formed
4. temperaturethe mixture was heated
5. temperatureto reflux
6. customover 2 hr
7. temperatureThe reaction mixture was refluxed overnight
8. temperatureto reflux again for 6 hr
9. customThe reaction was then quenched with 1N HCl
10. concentrationthe reaction concentrated in vacuo
11. extractionExtraction with CH2Cl2, aqueous workup, and column chromatography (n-hexane/ethyl acetate 8:1)

ORD-Eintrag

ord-2e0d9cf0e0e54777baa590e12151bfe3

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08129428B2