Triethylamine → 5-Norbornene 2-methylcinnamate

HRID 1982746노트

반응식

HRID 1982746 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.C(Cl)(=O)C=CC1C=CC=CC=1.[C:28]([O:31]CC)(=[O:30])[CH3:29]>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:29][C:28]([O-:31])=[O:30]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 660233-Phenylprop-2-enoyl chlorideHCID 78946Bicyclo(2.2.1)hept-5-ene-2-methanol

생성물 1

HCID 866064575-Norbornene 2-methylcinnamate수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

After 5-norbornene-2-methanol (15 g, 0.121 mol), which was synthesized as described above, triethylamine (Aldrich, 61.2 g, 0.605 mol), and 20 ml of THF were put into a 250 ml two-neck flask, agitation was conducted in an ice-water bath at 0° C. Cinnamoyl chloride (22.1 g, 0.133 mol) was dissolved in 60 ml THF, and then slowly added to the reactants using an additional flask. After 10 min, the reactants were heated to room temperature, and agitation was conducted for an additional time of 1 hour. The solution was diluted using ethyl acetate, moved to a separatory funnel, washed with water and NaHCO3 a few times, and distilled under reduced pressure to remove the solvent. Purification was conducted using column chromatography (hexane:ethyl acetate=20:1) to obtain a product. (yield: 88%)

후처리

  1. customwere put into a 250 ml two-neck flask
  2. customagitation was conducted in an ice-water bath at 0° C
  3. additionslowly added to the reactants
  4. customwas conducted for an additional time of 1 hour
  5. additionThe solution was diluted
  6. custommoved to a separatory funnel
  7. washwashed with water and NaHCO3 a few times
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customPurification
  11. customto obtain a product

출처 및 근거

ORD 기록
ord-b84af87ecc334d348788d61e61e7930d
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07541073B2

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