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Water → 2-Methyl-2-[(4-{2-[4-(phenylethynyl)phenoxy]ethyl}-1,3-thiazol-2-yl)thio]propionic acid methyl ester

HRID 914333
ノート
印刷プレビュー

反応式

HRID 914333 の反応式
[CH3:1][O:2][C:3](=[O:23])[C:4]([S:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=2)[N:12]=1)([CH3:6])[CH3:5].[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)#[CH:25].O>CN(C)C=O.C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:1][O:2][C:3](=[O:23])[C:4]([CH3:6])([S:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:25]#[C:24][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:18][CH:17]=2)[N:12]=1)[CH3:5]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 962WaterHCID 10821PhenylacetyleneHCID 597593322-({4-[2-(4-Iodophenoxy)ethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acid methyl ester

生成物 1

HCID 597592082-Methyl-2-[(4-{2-[4-(phenylethynyl)phenoxy]ethyl}-1,3-thiazol-2-yl)thio]propionic acid methyl ester収率 70.6%

試薬・触媒・溶媒 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 178418476HCID 178418476、化合物触媒
HCID 6228Dimethylformamide溶媒
HCID 8471Triethylamine溶媒

反応条件

温度
60 °C

実験手順

Under nitrogen atmosphere, 2-({4-[2-(4-iodophenoxy)ethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acid methyl ester (600 mg) synthesized in Example 144-2 and ethynylbenzene (145 mg) were dissolved in N,N-dimethylformamide (2 mL) and triethylamine (6 mL), dichlorobis(triphenylphosphine)palladium (10 mg) and copper(I) iodide (5 mg) were added, and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was cooled, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=5:1) to give the title compound (400 mg) as a yellow oil.

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-f3acbdde4e3241a48f7c5edec2419659
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08026370B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート