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Diisopropylamine → methyl (Z)-[4-[3-(4-tert-butyl-phenyl)-3-[4-[3-(pyrazol-1-yl)propynyl]phenyl]allyloxy]-2-methylphenoxy]acetate

HRID 1039505
ノート
印刷プレビュー

反応式

HRID 1039505 の反応式
[CH2:1]([N:4]1C=CC=N1)[C:2]#C.C(NC(C)C)(C)C.[C:16]([C:20]1[CH:25]=[CH:24][C:23](/[C:26](/[C:42]2[CH:47]=[CH:46][C:45]([C:48]#[C:49][CH2:50][N:51]3[CH2:56]COCC3)=[CH:44][CH:43]=2)=[CH:27]/[CH2:28][O:29][C:30]2[CH:40]=[CH:39][C:33]([O:34][CH2:35][C:36]([OH:38])=O)=[C:32]([CH3:41])[CH:31]=2)=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].[O:57]1CCC[CH2:58]1>[Cu]I>[C:16]([C:20]1[CH:21]=[CH:22][C:23](/[C:26](/[C:42]2[CH:47]=[CH:46][C:45]([C:48]#[C:49][CH2:50][N:51]3[CH:56]=[CH:2][CH:1]=[N:4]3)=[CH:44][CH:43]=2)=[CH:27]/[CH2:28][O:29][C:30]2[CH:40]=[CH:39][C:33]([O:34][CH2:35][C:36]([O:57][CH3:58])=[O:38])=[C:32]([CH3:41])[CH:31]=2)=[CH:24][CH:25]=1)([CH3:19])([CH3:18])[CH3:17]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 8028TetrahydrofuranHCID 117685231-(prop-2-yn-1-yl)-1H-pyrazoleHCID 23633559(Z)-[4-[3-(4-tert-Butylphenyl)-3-[4-[3-(morpholin-4-yl)propynyl]phenyl]allyloxy]-2-methylphenoxy]acetic Acid

生成物 1

HCID 86629317methyl (Z)-[4-[3-(4-tert-butyl-phenyl)-3-[4-[3-(pyrazol-1-yl)propynyl]phenyl]allyloxy]-2-methylphenoxy]acetate

試薬・触媒・溶媒

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

実験手順

N-Propargylpyrazole (130 mg, 1.23 mmol) and diisopropylamine (0.40 mL, 2.85 mmol) were added to a solution of methyl (Z)-[4-[3-(4-tert-butylphenyl)-3-(4-iodophenyl)allyloxy]-2-methylphenoxy]cetate (350 mg, 0.614 mmol; prepared as described in example 30) in tetrahydrofuran (10 mL). The mixture was degassed and copper(I) iodide (10 mg, 0.053 mmol) and bis(triphenylphosphine)alladium(II) dichloride (22 mg, 0.031 mmol) were added. The reaction mixture was stirred at ambient temperature over night, filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 4:1-3:1) yielding methyl (Z)-[4-[3-(4-tert-butylphenyl)-3-[4-[3-(pyrazol-1-yl)propynyl]phenyl]allyloxy]-2-methyl-phenoxy]acetate as brown oil.

後処理

  1. customThe mixture was degassed
  2. filtrationfiltered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 4:1-3:1)

出典と根拠

ORDレコード
ord-27201ec73ece4fc39f2fa518eb07e64c
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08551993B2

反応ノート

読み込み中…

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