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

HRID 1175599

反応式

HRID 1175599 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-625976f5c7e14f1eb31d20094c375f61
出典データセット
uspto-grants-2010_11
特許番号
US07842324B2

関連ノート

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