1-Bromopentane → Pentyl 4-methoxy-3-pentyloxycinnamate

HRID 850446

반응식

HRID 850446 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:5]=[CH:6][C:7]([OH:9])=[O:8].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:14][O:13][C:12]1[CH:11]=[CH:10][C:4]([CH:5]=[CH:6][C:7]([O:9][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:8])=[CH:3][C:2]=1[O:1][CH2:11][CH2:12][CH2:2][CH2:3][CH3:4]

참가 물질

5

반응물 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 921263-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acid

생성물 1

HCID 54536911Pentyl 4-methoxy-3-pentyloxycinnamate수율 217.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

3-Hydroxy-4-methoxycinnamic acid (9.7 g, 0.050 mol, 1.0 eq) was dissolved in DMF (90 ml). 1-Bromopentane (22.7 g, 0.150 mol, 3.0 eq) and anhydrous potassium carbonate (41.5 g, 0.30 mol, 6.0 eq) were successively added to this solution, and the mixture was stirred under heating at 90° C. for 3 hours. This reaction mixture was cooled to room temperature, and anhydrous potassium carbonate was filtered off. Water (200 ml) was added to the filtrate, and the mixture was exracted twice with ethyl acetate (200 ml). The organic layers were combined, washed with saturated brine (300 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (n-hexane/ethyl acetate=15/1-10/1) to give pentyl 4-methoxy-3-pentyloxycinnamate (18.2 g, 100%) as a colorless oil.

후처리

  1. temperatureThis reaction mixture was cooled to room temperature
  2. filtrationanhydrous potassium carbonate was filtered off
  3. additionWater (200 ml) was added to the filtrate
  4. washwashed with saturated brine (300 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe drying agent was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by column chromatography (n-hexane/ethyl acetate=15/1-10/1)

출처 및 근거

ORD 기록
ord-d0b1d754534f478bbff696545eb58029
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06017919

연결된 노트

불러오는 중…