Reaktion #86629

Reaktionsgleichung

5-Hexen-1-ol

triethylamine

2-bromoisobutyryl bromide

→

5-hexenyl 2-bromo-2-methylpropanate

Ausbeute 70.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction liquid
2. 2
   workup.WAITat room temperature for 15 hours
3. 3
   SonstigeThe reaction liquid
4. 4
   Filtrationwas then filtered
5. 5
   Einengenconcentrated with an evaporator
6. 6
   workup.DISSOLUTIONdissolved in diethyl ether (300 mL)
7. 7
   WaschenThe solution was washed with a 1N hydrochloric acid solution (2×300 mL)
8. 8
   workup.DISTILLATIONa saturated sodium bicarbonate solution (2×300 mL), and distilled water (2×300 mL)
9. 9
   TrocknenAfter that, the organic layer was dried over sodium sulfate
10. 10
    Filtrationfiltered
11. 11
    Einengenconcentrated with an evaporator
12. 12
    SonstigeThe product was then purified through a silica gel column (developing solvent: hexane/ethyl acetate=15/1)
13. 13
    Einengenconcentrated

Vorschrift

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).

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