Pyridine → 2-bromoethyl octanoate

2-Bromoethanol (4 g, 32 mmol) was added dropwise to a solution of octanoyl chloride (7.8 g, 48 mmol) and pyridine (5 mL) in benzene (50 mL). The reaction mixture was stirred at room temperature for 24 hours. After evaporation of benzene and pyridine under high vacuum, the residue was redissolved in benzene (100 mL). The solution was washed with water (50 mL), sulfuric acid solution (3×25 mL, 0.5N), sodium bicarbonate solution (25 mL, 1N), and water (2×75 mL). The benzene layer was dried over Na2SO4. The drying agent was suction filtered, and the benzene was evaporated. The resulting oil was purified by silica gel chromatography using chloroform/methanol (9:1) to give 6.5 g of pure product. Yield 81%; liquid; IR (neat) 2930 and 2850 (aliphatic CH), 1730 (CO ester) cm-1 ; 1H NMR (CDCl3) 0.85-0.95 (t, CH3 (CH2)4), 1.20-1.40 (m, CH3 (CH2)4), 1.55-1.70 (m, CH2 CH2 CO), 2.25-2.40 (t, CH2 CH2 CO), 3.50-3.60 (t, O CH2 CH2 Br), 4.35-4.40 (t, O CH2 CH2 Br).

1. customAfter evaporation of benzene and pyridine under high vacuum
2. dissolutionthe residue was redissolved in benzene (100 mL)
3. washThe solution was washed with water (50 mL), sulfuric acid solution (3×25 mL, 0.5N), sodium bicarbonate solution (25 mL, 1N), and water (2×75 mL)
4. dry with materialThe benzene layer was dried over Na2SO4
5. filtrationfiltered
6. customthe benzene was evaporated
7. customThe resulting oil was purified by silica gel chromatography

ORD record

ord-f059476046b2459ea37b4e42da564690

Source dataset

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05679684