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 1 hour. After cooling to 0 degrees, a solution of 5-bromo-3-furaldehyde (2.42 g, 14 mmol) in tetrahydrofuran (3 ml) was added and conditions maintained for 20 minutes. The mixture was further cooled to -78 degrees 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 minutes. Stirring was continued overnight (12 hours) 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 1 hour
2. temperatureAfter cooling to 0 degrees
3. temperatureconditions maintained for 20 minutes
4. temperatureThe mixture was further cooled to -78 degrees
5. addition9.77 ml, 1.67 mmol) was added dropwise
6. custom(12 hours)
7. customwhile the cooling bath attained room temperature
8. customThe mixture was quenched with saturated aqueous ammonium chloride
9. additiondiluted with water (15 ml)
10. extractionextracted with ethyl ether
11. customEvaporation of the
12. dry with materialdried (magnesium sulfate)
13. extractionextract
14. customgave a brown oil, which
15. customchromatographed on silica using 15% ethyl ether/petroleum ether
16. customFractions with Rf of about 0.25 on evaporation

ORD record

ord-813c2d49783749c4bf45635d8d25be45

Source dataset

uspto-grants-1992_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05171863