Triethylamine → Hex-5-EN-1-YL 2-bromo-2-methylpropanoate

5-Hexen-1-ol (42.6 g), triethylamine (45.8 g), and tetrahydrofuran (0.8 L) were mixed. After ice cooling, 2-bromoisobutyryl bromide (100 g) was dropped. The reaction liquid was stirred at 4° C. for 3 hours, and then at room temperature for 15 hours. The reaction liquid was then filtered, concentrated with an evaporator, and dissolved in diethyl ether (300 mL). The solution was washed with a 1N hydrochloric acid solution (2×300 mL), a saturated sodium bicarbonate solution (2×300 mL), and distilled water (2×300 mL), in this order. After that, the organic layer was dried over sodium sulfate, filtered, and concentrated with an evaporator. The product was then purified through a silica gel column (developing solvent: hexane/ethyl acetate=15/1), and concentrated to give 74.2 g of 5-hexenyl 2-bromo-2-methylpropanate of the following chemical formula (compound 1).

1. customThe reaction liquid
2. waitat room temperature for 15 hours
3. customThe reaction liquid
4. filtrationwas then filtered
5. concentrationconcentrated with an evaporator
6. dissolutiondissolved in diethyl ether (300 mL)
7. washThe solution was washed with a 1N hydrochloric acid solution (2×300 mL)
8. distillationa saturated sodium bicarbonate solution (2×300 mL), and distilled water (2×300 mL)
9. dry with materialAfter that, the organic layer was dried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated with an evaporator
12. customThe product was then purified through a silica gel column (developing solvent: hexane/ethyl acetate=15/1)
13. concentrationconcentrated

ORD record

ord-b22f08d90f174701a059f2bb7641776a

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434794B2