Chloride → 5-Norbornene 2-methylcinnamate

HRID 539388

반응식

HRID 539388 반응식
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH2:8]O.C(N(CC)CC)C.[Cl-].[C:18]([O:21]CC)(=[O:20])[CH3:19]>C1COCC1>[CH:1]12[CH2:7][CH:4]([CH:3]=[CH:2]1)[CH2:5][CH2:6]2.[CH3:8][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH:7]=[CH:19][C:18]([O-:21])=[O:20]

참가 물질

6

반응물 4

HCID 312ChlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 78946Bicyclo(2.2.1)hept-5-ene-2-methanol

생성물 1

HCID 866064575-Norbornene 2-methylcinnamate수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

15 g (0.121 mol) of the 5-norbornene-2-methanol prepared in Example 1, 61.2 g (0.605 mol) of triethylamine (produced from Aldrich Inc.), and 20 ml of THF were loaded into a 250 ml 2-neck flask and then stirred at 0° C. in an ice-water bath. 22.1 g (0.133 mol) of cinamoil chloride dissolved in 60 ml of THF was slowly added to the prepared mixture using an additional flask for 10 minutes. Then, the temperature of the reactant was increased to room temperature and then stirred for one hour. The resulting solution was diluted using an ethyl acetate. The diluted solution was loaded into a separatory funnel, washed using water and NaHCO3 several times, and then distilled in at a reduced pressure to remove a solvent. The result was refined using a column chromatography (Hexane: Ethyl acetate=20:1) to attain a product. (Yield: 88%)

후처리

  1. additionwas slowly added to the prepared mixture
  2. customfor 10 minutes
  3. temperatureThen, the temperature of the reactant was increased to room temperature
  4. stirringstirred for one hour
  5. additionThe resulting solution was diluted
  6. customThe diluted solution was loaded into a separatory funnel
  7. washwashed
  8. distillationdistilled in at a reduced pressure
  9. customto remove a solvent

출처 및 근거

ORD 기록
ord-b12ebf1f8c3b405fb78ffbe9a5a21978
출처 데이터셋
uspto-grants-2014_10
특허 번호
USRE045219E1

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