反应详情

A mixture of 1-bromooctane (1.33 g, 6.9 mmol) and magnesium turnings (174 mg, 7.3 mmol) in tetrahydrofuran (8 ml) was refluxed under argon for 60 minutes. After cooling to 0°, a solution of 5-bromo-3-furaldehyde (1.21 g, 6.9 mmol) in THF (1 ml) was added and conditions maintained for 60 min. The mixture was further cooled to -78° and tert-butyl lithium (a 1.7M solution in pentane, 4.26 ml, 7.3 mmol) was added dropwise, followed by chlorotrimethylsilane (2.63 ml, 20.7 mmol) after 1 hour. Stirring was continued overnight while the cooling bath attained room temperature. The mixture was quenched with saturated aqueous ammonium chloride, diluted with water (15 ml) and extracted with ether. Evaporation of the dried (magnesium sulfate) extract gave a brown oil, which was subjected to flash chromatography on silica using 15% ethyl ether/petroleum ether. Fractions with Rf of about 0.2 on evaporation gave the captioned compound as a yellow oil.

1. temperaturewas refluxed under argon for 60 minutes
2. temperatureAfter cooling to 0°
3. temperatureconditions maintained for 60 min
4. temperatureThe mixture was further cooled to -78°
5. customThe mixture was quenched with saturated aqueous ammonium chloride
6. additiondiluted with water (15 ml)
7. extractionextracted with ether
8. customEvaporation of the
9. dry with materialdried (magnesium sulfate)
10. extractionextract
11. customgave a brown oil, which
12. customFractions with Rf of about 0.2 on evaporation