Toluene → Ethyl 4-(4'-nitro-1,1'-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate

HRID 30837

반응식

HRID 30837 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:24])[CH2:9][CH:10]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.[N+:25]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)([O-:27])=[O:26].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[N+:25]([C:28]1[CH:33]=[CH:32][C:31]([C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:24])[CH2:9][CH:10]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=2)=[CH:30][CH:29]=1)([O-:27])=[O:26]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27735524-Nitrophenylboronic acidHCID 21985805Ethyl 4-(4-bromophenyl)-4-oxo-2-(2-phenylethyl)butanoate

생성물 1

HCID 21985737Ethyl 4-(4'-nitro-1,1'-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate수율 75.2%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
85 °C

실험 절차

Ethyl 4-(4-bromophenyl)-4-oxo-2-(2-phenylethyl)butanoate (4.32 g, 11.1 mmol) and 4-nitrophenylboronic acid (2.22, 13.3 mmol) was added to a dry flask under argon. Toluene (100 mL), dioxane (25 mL), saturated aqueous sodium carbonate (30 mL), and [1,1′-bis(diphenyl-phosphino)-ferrocene]dichloro palladium(II) (1:1 complex with dichloromethane, 453 mg, 0.55 mmol) were added and the mixture was thoroughly degassed. The resulting mixture was then heated at 85° C. for 16 h before it was cooled to rt. Water was added and the mixture was extracted twice with ethyl acetate. The combined extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (Biotage flash 75, 5:1 ethyl acetate/hexane) to afford ethyl 4-(4′-nitro-1,1′-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate (3.6 g, 75%). HPLC ret. time 3.99 min, 1H NMR (300 MHz, CDCl3) δ 1.29 (t, 3H), 1.85-2.08 (m, 2H), 2.71 (t, 2H), 3.05-3.20 (m, 2H), 3.45-3.52 (m, 1H), 4.20 (q, 2H), 7.18-7.31 (m, 5H), 7.72 (d, 2H), 7.78 (d, 2H), 8.05 (d, 2H), 8.33 (d, 2H).

후처리

  1. customthe mixture was thoroughly degassed
  2. temperaturewas cooled to rt
  3. additionWater was added
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (Biotage flash 75, 5:1 ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-93556e30d18b41e9bd7834bdc4a200d8
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423156B2

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