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

HRID 58351
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HRID 58351 반응식
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].C(N(CC)CC)C.[Br:15][C:16]([CH3:21])([CH3:20])[C:17](Br)=[O:18]>O1CCCC1>[Br:15][C:16]([CH3:21])([CH3:20])[C:17]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6])=[O:18]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 699635-Hexen-1-olHCID 886852-Bromo-2-methylpropionyl bromide

생성물 1

HCID 20829612Hex-5-EN-1-YL 2-bromo-2-methylpropanoate수율 70%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
4 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b22f08d90f174701a059f2bb7641776a
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09434794B2

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