Potassium Carbonate → 4-[4-(Allyloxy)phenoxy]benzaldehyde

HRID 1370827

반응식

HRID 1370827 반응식
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10]([O:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[CH:11]=[CH2:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)C>[CH2:10]([O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:16][CH:15]=1)[CH:11]=[CH2:12]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 17138834-(Allyloxy)phenol

생성물 1

HCID 185121824-[4-(Allyloxy)phenoxy]benzaldehyde수율 81%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

4-Fluorobenzaldehyde (3.8 mL, 35.1 mmoles) was added to a solution of the product from Example 60A (4.39 g, 29.3 mmoles) and K2CO3 (8.90 g, 64.4 mmoles) in DMF (29.3 mL). The resulting mixture was heated to 100° C. for 2.5 days and then cooled to room temperature. The crude products were diluted with diethyl ether, extracted with sat. NH4Cl, extracted with H2O (2×), washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography on a prepacked Biotage column (hexane→9:1 hexane:ethyl acetate) on silica gel to provide the title compound (3.50 g, 81%) as a clear colorless oil.

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with sat. NH4Cl
  3. extractionextracted with H2O (2×)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on a prepacked Biotage column (hexane→9:1 hexane:ethyl acetate) on silica gel

출처 및 근거

ORD 기록
ord-6ec84693bfce4f2ba7bac6e36062ed87
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06583180B2

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