Chlorotrimethylsilane → 3-(1-Hydroxytridecyl)-5-trimethylsilylfuran

A mixture of 1-bromododecane (3.45 g, 14 mmol) and magnesium turnings (349 mg, 14.5 mmol) in tetrahydrofuran (10 ml) was refluxed under argon for 1h. After cooling to 0°, a solution of 5-bromo-3-furaldehyde (2.42 g, 14 mmol) in tetrahydrofuran (3 ml) was added and conditions maintained for 20 min. The mixture was further cooled to -78° and tert-butyl lithium (a 1.7M solution in pentane; 9.77 ml, 1.67 mmol) was added dropwise, followed by chlorotrimethylsilane (5.27 ml, 41.5 mmol) after 20 min. Stirring was continued overnight (12h) while the cooling bath attained room temperature. The mixture was quenched with saturated aqueous ammonium chloride, diluted with water (15 ml) and extracted with ethyl ether. Evaporation of the dried (magnesium sulfate) extract gave a brown oil, which was flash chromatographed on silica using 15% ethyl ether/petroleum ether. Fractions with Rf of about 0.25 on evaporation afforded the title trimethylsilylfuran as a pale yellow oil.

1. temperaturewas refluxed under argon for 1h
2. temperatureAfter cooling to 0°
3. temperatureconditions maintained for 20 min
4. temperatureThe mixture was further cooled to -78°
5. addition9.77 ml, 1.67 mmol) was added dropwise
6. customwhile the cooling bath attained room temperature
7. customThe mixture was quenched with saturated aqueous ammonium chloride
8. additiondiluted with water (15 ml)
9. extractionextracted with ethyl ether
10. customEvaporation of the
11. dry with materialdried (magnesium sulfate)
12. extractionextract
13. customgave a brown oil, which
14. customchromatographed on silica using 15% ethyl ether/petroleum ether
15. customFractions with Rf of about 0.25 on evaporation

ORD record

ord-34c7522bce8443e1a316e4ef19e41e08

Source dataset

uspto-grants-1992_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05134128