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Tetrahydrofuran → methyl (Z)-[2-methyl-4-[3-(4-methylphenyl)-3-[4-(3-pyrazol-1-ylpropynyl)phenyl]allyloxy]phenoxy]acetate

HRID 549843
ノート
印刷プレビュー

反応式

HRID 549843 の反応式
[CH3:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14]/[CH:15]=[C:16](/[C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)\[C:17]2[CH:22]=[CH:21][C:20]([C:23]#[C:24][CH2:25][N:26]3CCO[CH2:28][CH2:27]3)=[CH:19][CH:18]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.C([N:42]1[CH:46]=CC=N1)C#C.[O:47]1CCC[CH2:48]1>C(N(CC)CC)C.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.[Cu]I>[CH3:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14]/[CH:15]=[C:16](/[C:32]2[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=2)\[C:17]2[CH:22]=[CH:21][C:20]([C:23]#[C:24][CH2:25][N:26]3[CH:27]=[CH:28][CH:46]=[N:42]3)=[CH:19][CH:18]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([O:47][CH3:48])=[O:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 8028TetrahydrofuranHCID 117685231-(prop-2-yn-1-yl)-1H-pyrazoleHCID 23633919(Z)-[2-Methyl-4-[3-(4-methylphenyl)-3-[4-[3-(morpholin-4-yl)propynyl]phenyl]allyloxy]-phenoxy]acetic Acid

生成物 1

HCID 86629289methyl (Z)-[2-methyl-4-[3-(4-methylphenyl)-3-[4-(3-pyrazol-1-ylpropynyl)phenyl]allyloxy]phenoxy]acetate

試薬・触媒・溶媒 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 178418397HCID 178418397、化合物触媒
HCID 8471Triethylamine溶媒

実験手順

A solution of methyl (Z)-[2-methyl-4-[3-(4-iodophenyl)-3-(4-methylphenyl)]allyloxy]-phenoxy]acetate (310 mg, 0.587 mmol; example 3) in a mixture of tetrahydrofuran (9 mL) and triethylamine (9 mL) was degassed and 1-propargyl-1H-pyrazole (124 mg, 1.17 mmol) was added in argon atmosphere. The solution was cooled down; tetrakis(triphenylphosphine)palladium (54 mg, 0.046 mmol) and copper(I) iodide (17.8 mg, 0.094 mmol) were added. The reaction mixture was stirred at ambient temperature for 4 days, subsequently evaporated in vacuo and the residue was dissolved in ethyl acetate (20 mL). The solution was washed with water (3×15 mL), dried with anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 7:3) yielding methyl (Z)-[2-methyl-4-[3-(4-methylphenyl)-3-[4-(3-pyrazol-1-ylpropynyl)phenyl]allyloxy]phenoxy]acetate.

後処理

  1. customwas degassed
  2. temperatureThe solution was cooled down
  3. customsubsequently evaporated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate (20 mL)
  5. washThe solution was washed with water (3×15 mL)
  6. dry with materialdried with anhydrous magnesium sulphate
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 7:3)

出典と根拠

ORDレコード
ord-15d396c409034ec3875c66c2eeadd499
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07943613B2

反応ノート

読み込み中…

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