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

HRID 375995

반응식

HRID 375995 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 977Oxygen용매

실험 절차

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°).

후처리

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

출처 및 근거

ORD 기록
ord-00b5aedde9b640c795ea84266ba6a003
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05488135

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