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Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(4-pyridylethynyl)cyclohexan-1-one

HRID 343556
ノート
印刷プレビュー

反応式

HRID 343556 の反応式
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[C:26][C:27]4[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=4)[CH2:20][CH2:19][C:18]4(OCC[O:21]4)[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[C:26][C:27]4[CH:28]=[CH:29][N:30]=[CH:31][CH:32]=4)[CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH2:20]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 544017964-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(4-pyridylethynyl)-1,1-(ethylenedioxy)cyclohexane

生成物 1

HCID 542175994-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(4-pyridylethynyl)cyclohexan-1-one収率 91%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962
Water
溶媒

実験手順

A mixture of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(4-pyridylethynyl)-1,1-(ethylenedioxy)cyclohexane (0.10 g, 0.24 mmol) and pyridinium p-toluenesulfonate (0.06 g, 0.24 mmol) in acetone (4 mL) and water (1 mL) was refluxed for 20 h., then was evaporated. Water was added, the mixture was extracted three times with dichloromethane, was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 35:65 ethyl acetate:hexanes, provided 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(4-pyridylethynyl)cyclohexan-1-one (0.08 g, 91%) as a white solid, mp 148°-149° C. Anal. (C25H27NO3.0.5 H2O) calcd: C, 75.29; H, 7.08; N, 3.51; found: C, 75.51; H, 6.95; N, 3.42.

後処理

  1. temperaturewas refluxed for 20 h.
  2. customwas evaporated
  3. additionWater was added
  4. extractionthe mixture was extracted three times with dichloromethane
  5. dry with materialwas dried (magnesium sulfate)
  6. customwas evaporated
  7. customPurification by flash chromatography
  8. washeluting with 35:65 ethyl acetate

出典と根拠

ORDレコード
ord-6589915f71da445b8796580df9b7fdea
出典データセット
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05861421

反応ノート

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