Chlorotrimethylsilane → 4-(1-Hydroxynonyl)-2-trimethylsilylfuran

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 min. 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 1h. 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 0.2 on evaporation gave the captioned compound as a yellow oil.

1. temperaturewas refluxed under argon for 60 min
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 0.2 on evaporation

ORD record

ord-a17000d9939544af872847d5d8b93c2a

Source dataset

uspto-grants-1992_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05134128