Potassium Carbonate → Ethyl 2-(2-methoxy-5'-(methoxymethyl)biphenyl-4-yl)acetate

HRID 1175599

반응식

HRID 1175599 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:6]=[CH:7][C:8]=1OS(C(F)(F)F)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[CH3:29][O:30][CH2:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1>COCCOC.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:6]=[CH:7][C:8]=1[C:34]1[CH:33]=[C:32]([CH2:31][O:30][CH3:29])[CH:37]=[CH:36][CH:35]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 38258553-(Methoxymethyl)benzeneboronic acidHCID 58820079Ethyl (3-methoxy-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)acetate

생성물 1

HCID 68774497Ethyl 2-(2-methoxy-5'-(methoxymethyl)biphenyl-4-yl)acetate수율 76%

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

To a solution of Ethyl 2-(3-methoxy-4-(trifluoromethylsulfonyloxy)phenyl)acetate (example 27d) (2 g, 5.8 mmol) in DME (36 mL) and water (9 mL) was added potassium carbonate (1.61 g, 11.6 mmol) and 3-(methoxymethyl)phenylboronic acid (962 mg, 5.8 mmol) and the mixture was degassed using argon stream for 30 minutes. Pd[PPh3]4 (330 mg, 0.29 mmol) was added and the mixture was heated at 80° C. under argon overnight. The solvents were removed under reduced pressure and the residue extracted with EtOAc, washed with water and brine, dried over MgSO4, filtered and evaporated. The residue was purified on silica gel (20% EtOH/hexanes) to yield 1.38 g (76%) of ethyl 2-(2-methoxy-5′-(methoxymethyl)biphenyl-4-yl)acetate. 1H NMR(400 MHz, dMSO): δ 1.16-1.20 (t, 3H), 3.27 (s, 3H), 3.68 (s, 2H), 3.72 (s, 3H), 4.06-4.11 (q, 2H) 4.41 (s, 2H) 6.89 (d, 1H), 7.00 (s, 1H) 7.19-7.24 (m, 2H), 7.34-7.36 (m, 3H).

후처리

  1. customthe mixture was degassed
  2. customfor 30 minutes
  3. customThe solvents were removed under reduced pressure
  4. extractionthe residue extracted with EtOAc
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified on silica gel (20% EtOH/hexanes)

출처 및 근거

ORD 기록
ord-625976f5c7e14f1eb31d20094c375f61
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842324B2

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