Water → methyl (Z)-3-(3'-amino-2-butoxybiphenyl-4-yl)-2-methoxyacrylate

HRID 390692ノート

反応式

HRID 390692 の反応式
C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=1.[CH2:18]([O:22][C:23]1[CH:24]=[C:25](/[CH:30]=[C:31](\[O:36][CH3:37])/[C:32]([O:34][CH3:35])=[O:33])[CH:26]=[CH:27][C:28]=1I)[CH2:19][CH2:20][CH3:21].O>COCCOC.C1C=CC([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)=CC=1.C(OCC)(=O)C>[NH2:8][C:9]1[CH:10]=[C:11]([C:28]2[CH:27]=[CH:26][C:25](/[CH:30]=[C:31](\[O:36][CH3:37])/[C:32]([O:34][CH3:35])=[O:33])=[CH:24][C:23]=2[O:22][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:13][CH:14]=1

参加物

8

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27632413-Aminophenylboronic acid hydrochlorideHCID 59574929methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-methoxyacrylate

生成物 1

HCID 86626122methyl (Z)-3-(3'-amino-2-butoxybiphenyl-4-yl)-2-methoxyacrylate収率 93.8%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

11.2 mL (22.4 mmol) of aqueous 2 N potassium carbonate solution and 0.52 g (0.45 mmol) of tetrakis(triphenylphosphine)palladium are added to a solution of 1.87 g (10.8 mmol) of 3-aminophenylboronic acid hydrochloride and 3.5 g (9 mmol) of methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-methoxyacrylate (prepared according to Example 24c) in 70 mL of ethylene glycol dimethyl ether. The reaction mixture is heated at 100° C. for 4 hours. After addition of 30 mL of water and extraction with ethyl acetate, the organic phases are combined, washed with saturated sodium chloride solution and dried over sodium sulfate. The solvents are evaporated off and the residue is then purified by chromatography on a column of silica eluted with a 90/10 heptane/ethyl acetate mixture. 3 g (93%) of methyl (Z)-3-(3′-amino-2-butoxybiphenyl-4-yl)-2-methoxyacrylate are obtained in the form of a yellow oil.

後処理

  1. washwashed with saturated sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then purified by chromatography on a column of silica
  5. washeluted with a 90/10 heptane/ethyl acetate mixture

出典と根拠

ORDレコード
ord-4f9266252fc34994bf2d41c1de451922
出典データセット
uspto-grants-2013_02
特許番号
US08383652B2

反応ノート

読み込み中…