Benzene → 5-[2-(2,5-Dimethoxyphenyl)ethinyl]-2-hydroxybenzoic acid methyl ester

HRID 375995

反応式

HRID 375995 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11]#[CH:12].I[C:14]1[CH:23]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[C:17]([OH:24])=[CH:16][CH:15]=1.C1C=CC=CC=1.C(N(CC)CC)C>O=O.[Cu]I>[CH3:22][O:21][C:19](=[O:20])[C:18]1[CH:23]=[C:14]([C:12]#[C:11][C:4]2[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH:15]=[CH:16][C:17]=1[OH:24]

参加物

7

反応物 4

HCID 241BenzeneHCID 8471TriethylamineHCID 248910Methyl 5-IodosalicylateHCID 110949512,5-Dimethoxyphenylacetylene

生成物 1

HCID 153840065-[2-(2,5-Dimethoxyphenyl)ethinyl]-2-hydroxybenzoic acid methyl ester

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 977Oxygen溶媒

実験手順

Under argon atmosphere 240 mg of 2,5-dimethoxyphenylacetylene and 493 mg of methyl 5-iodosalicylate are dissolved in 20 ml of oxygen-free and dry benzene. The mixture is treated with 85 mg of tetrakis (triphenylphosphine)palladium, 20 mg of copper(I)iodide and 450 mg of triethylamine, stirred at room temperature overnight and then poured onto 100 ml of aqueous pH 7 buffer. After extraction with ethyl acetate and purification by chromatography on silicagel, 5-[2-(2,5-dimethoxyphenyl)ethinyl]-2-hydroxybenzoic acid methyl ester is obtained (colorless crystals of M.P. 105°-108°).

後処理

  1. additionpoured onto 100 ml of aqueous pH 7 buffer
  2. extractionAfter extraction
  3. customwith ethyl acetate and purification by chromatography on silicagel

出典と根拠

ORDレコード
ord-00b5aedde9b640c795ea84266ba6a003
出典データセット
uspto-grants-1996_01
特許番号
US05488135

関連ノート

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