Propyne → HCID 22602329, Verbindung

Temperatur

0 °C

Tetramethylethylenediamine (TMEDA) (15 ml) was added to a THF (80 ml) solution of propyne (about 4 g, 0.1 mol) under argon. To the mixture, n-BuLi (1.55 M, 64.5 ml, 100 mmols) was added dropwise at −78° C. With the temperature being raised gradually to 0° C., the mixture was stirred for 1.5 hours, and then cooled again to −78° C. Thereto, an HMPA-THF (20 ml+20 ml) solution of the 1-bromo-3-methyldodecane (5″) (13.2 g, 50 mmols) was added dropwise, and with the temperature of the mixture being raised gradually to room temperature, stirring was continued overnight. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, and extracted with hexane. The resulting organic layer was washed (water, a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride), dried (magnesium sulfate), and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 6-methyl-2-pentadecyne (6″) (12.1 g, 97%). 1H-NMR (90 MHz, CDCl3) 0.84 (3H,d,J=7,6-Me), 0.88 (3H,t,J=7,15-H), 1.0-1.6 (19H,m,5˜14-H), 1.77 (3H,t,J=2.5,1-H), 2.12 (2H,m,4-H).

1. temperaturecooled again to −78° C
2. temperaturewith the temperature of the mixture being raised gradually to room temperature
3. stirringstirring
4. waitwas continued overnight
5. extractionextracted with hexane
6. washThe resulting organic layer was washed (water
7. dry with materiala saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride), dried (magnesium sulfate)
8. concentrationconcentrated under reduced pressure
9. customThe resulting residue was purified by silica gel column chromatography

ORD-Eintrag

ord-bf57764a195b41289db301d74f6ab7b2

Quelldatensatz

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06835846B2