Pyridine → Undec-10-en-1-yl 2-bromo-2-methylpropanoate

A similar synthetic scheme was conducted as followed.x To a solution of 4.257 g (25 mmol) of co-undecylenyl alcohol in 25 mL of dry tetrahydrofuran was added 2.1 mL of pyridine (26.5 mmol) by dropwise addition of 3.10 mL of 2-bromoisobutyryl bromide (25 mmol). The mixture was stirred at ambient temperature for 8 hours. The remaining THF was removed under reduced pressure followed by dilution with hexane (50 mL). The mixture was washed with 2 M HCl solution and twice with water (50 ml). The organic phase was dried over sodium sulfate and filtered. The solvent was removed from the filtrate under reduced pressure yielding a colorless oil (89%). 1H NMR (500 MHz, CDCl3) δ: 1.22-1.45 (br m, 12H); 1.62-1.75 (m, 2H); 1.94 (s 6H); 2.05 (q, 2H, J) 6 Hz); 4.17 (t, 2H, J=9 Hz); 4.9-5.05 (m, 2H); 5.72-5.9 (m, 1H) ppm.

1. customThe remaining THF was removed under reduced pressure
2. washThe mixture was washed with 2 M HCl solution and twice with water (50 ml)
3. dry with materialThe organic phase was dried over sodium sulfate
4. filtrationfiltered
5. customThe solvent was removed from the filtrate under reduced pressure

ORD record

ord-cd2043722235401eac043cc945619b19

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09248467B2