Potassium Carbonate → 3-{4-[3-(Biphenyl-4-yloxy)-propoxy]-3-methoxy-phenyl}-2-methoxy-propionic acid ethyl ester

HRID 459153ノート

反応式

HRID 459153 の反応式
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([O:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([O:14][CH3:15])[CH:8]=1)[CH3:2].Br[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C.O>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([O:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:20][CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)=[C:9]([O:14][CH3:15])[CH:8]=1)[CH3:2]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 152334631,1'-Biphenyl, 4-(3-bromopropoxy)-HCID 588229863-(4-Hydroxy-3-methoxy-phenyl)-2-methoxy-propionic acid ethyl ester

生成物 1

HCID 588226693-{4-[3-(Biphenyl-4-yloxy)-propoxy]-3-methoxy-phenyl}-2-methoxy-propionic acid ethyl ester収率 59.7%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

To a solution of 3-(4-hydroxy-3-methoxy-phenyl)-2-methoxy-propionic acid ethyl ester (Example 132, Step A) (0.080 g, 0.31 mmol) in acetonitrile (10 mL) was added 4-(3-bromo-propoxy)biphenyl (Example 132, Step D) (0.101 g, 0.35 mmol) and potassium carbonate (0.115 g, 0.945 mmol). The resulting suspension was stirred at 85° C. overnight. After cooling, the reaction mixture was diluted with ethyl acetate (10 mL), and water (10 mL) was added. The organic layer was washed with water (10 mL) and brine (10 mL), dried (MgSO4), and concentrated. The crude product was purified by silica gel column chromatography (silica gel, hexanes/ethyl acetate, 7:3) to produce 3-{4-[3-(biphenyl-4-yloxy)-propoxy]-3-methoxy-phenyl}-2-methoxy-propionic acid ethyl ester (0.086 g, 59%). 1H-NMR (200.15 MHz, CDCl3): δ 7.57–7.26 (m, 7H), 6.98 (d, 2H, J=8.6), 6.87–6.73 (m, 3H), 4.25–4.17 (m, 6H), 3.91 (dd, 1H, J=7.0, 5.6), 3.83 (s, 3H), 3.35 (s, 3H), 2.97–2.93 (m, 2H), 2.31 (qn, 2H, J=5.9), 1.24 (t, 3H, J=7.3).

後処理

  1. temperatureAfter cooling
  2. additionwas added
  3. washThe organic layer was washed with water (10 mL) and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column chromatography (silica gel, hexanes/ethyl acetate, 7:3)

出典と根拠

ORDレコード
ord-75281f50a40141ddbc3ccc52fc4b871f
出典データセット
uspto-grants-2007_03
特許番号
US07192982B2

反応ノート

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