Lithium Hydroxide → [4-(4-Methoxy-4''-trifluoromethoxy-[1,1';3',1'']terphenyl-5'-ylmethoxy)-2-methyl-phenoxy]-acetic acid

HRID 19503

反応式

HRID 19503 の反応式
Br[C:2]1[CH:3]=[C:4]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25]C)=[C:20]([CH3:27])[CH:19]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH:7]=1.[F:28][C:29]([F:41])([F:40])[O:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.[C:42](=[O:45])([O-])[O-:43].[K+].[K+].[OH-].[Li+]>O1CCOCC1.C1(P([Pd](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C.O>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[CH:5]=[C:4]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:42]([OH:43])=[O:45])=[C:20]([CH3:27])[CH:19]=3)[CH:3]=[C:2]([C:34]3[CH:35]=[CH:36][C:31]([O:30][C:29]([F:41])([F:40])[F:28])=[CH:32][CH:33]=3)[CH:7]=2)=[CH:13][CH:12]=1

参加物

9

反応物 4

HCID 3939Lithium HydroxideHCID 11430Potassium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 691074205-Bromo-3-(4-ethoxy-3-methyl-phenoxymethyl)-4'-methoxy-biphenyl

生成物 1

HCID 11599107[4-(4-Methoxy-4''-trifluoromethoxy-[1,1';3',1'']terphenyl-5'-ylmethoxy)-2-methyl-phenoxy]-acetic acid

試薬・触媒・溶媒 4

HCID 178420554HCID 178420554、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

5-Bromo-3-(4-ethoxy-3-methyl-phenoxymethyl)-4′-methoxy-biphenyl 15 (50 mg, 0.11 mmol) and 4-trifluoromethoxyphenylboronic acid (30 mg, 0.15 mmol, 1.3 equiv.) are dissolved in dioxane (0.5 mL). Potassium carbonate (38 mg, 0.27 mmol), water (0.05 mL) and ethanol (0.05 mL) are added, followed by tetrakis (triphenylphosphino)palladium (15.6 mg, 0.13 mmol). The mixture is stirred under nitrogen and subjected to microwave (170° C. for 10 min). Cooling, addition of 0.25 mL of aqueous 1N lithium hydroxide solution, and stirring for 3 hours at room temperature, followed by reversed-phase purification yielded [4-(4-methoxy-4″-trifluoromethoxy-[1,1′;3′,1″]terphenyl-5′-ylmethoxy)-2-methyl-phenoxy]-acetic acid A2. 1H-NMR (400 MHz, CDCl3) δ=7.50 (m, 3H), 7.42 (m, 4H), 7.17 (d, J=8.0 Hz, 2H), 6.87 (d, J=8.0 Hz, 2H), 6.75 (d, J=2.8 Hz, 1H), 6.65 (dd, J=8.8, 2.8 Hz, 1H), 6.58 (d, J=8.8 Hz, 1H), 5.17 (s, 2H), 4.50 (s, 2H), 3.73 (s, 3H), 2.16 (s, 3H). 19F-NMR (376 MHz, CDCl3) δ=−57.8. MS calculated for C30H26F3O6 (M+H+) 539.17. found 539.0.

後処理

  1. custom(170° C. for 10 min)
  2. temperatureCooling
  3. stirringstirring for 3 hours at room temperature
  4. customfollowed by reversed-phase purification

出典と根拠

ORDレコード
ord-23ddb7be655f4c35a298c86d3c047f61
出典データセット
uspto-grants-2010_06
特許番号
US07745445B2

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