Water → 2-[4-(4-Propylcyclohexyl)phenyl]selenophene

HRID 1873386

反応式

HRID 1873386 の反応式
I[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[CH2:7]([CH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)[CH2:8][CH3:9].C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.C(O)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>[CH2:7]([CH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19]([C:2]3[Se:3][CH:4]=[CH:5][CH:6]=3)=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)[CH2:8][CH3:9]

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 1421832-IodoselenopheneHCID 31047104-(trans-4-Propylcyclohexyl)phenylboronic Acid

生成物 1

HCID 594562962-[4-(4-Propylcyclohexyl)phenyl]selenophene

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 21863594Toluene ethanol溶媒

実験手順

A mixture 0111.0 g (41.1 mmol) of 2-iodoselenophene, 7.98 g (32.4 mmol) of 4-(4-propylcyclohexyl)phenylboronic acid, 3.70 g (3.20 mmol) of tetrakis(triphenylphosphine)palladium(0) and 60 ml of 2 N sodium carbonate soln. in 160 ml of toluene/ethanol (1:1) is heated under reflux for 22 h. After cooling, water is added, and the batch is extracted a number of times with MTBE. The combined organic phases are washed with water, sat. sodium hydrogencarbonate soln., 1 N hydrochloric acid and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:EtOAc=20:1). The further purification is carried out by recrystallisation from n-heptane; 2-[4-(4-propylcyclohexyl)phenyl]selenophene is obtained as a colourless solid.

後処理

  1. temperatureunder reflux for 22 h
  2. temperatureAfter cooling
  3. extractionthe batch is extracted a number of times with MTBE
  4. washThe combined organic phases are washed with water, sat. sodium hydrogencarbonate soln
  5. customThe solution is dried
  6. concentrationconcentrated to dryness
  7. customThe residue is purified by column chromatography (SiO2, n-heptane:EtOAc=20:1)
  8. customThe further purification
  9. customis carried out by recrystallisation from n-heptane

出典と根拠

ORDレコード
ord-76e1073097df4d6c889c3db6f8abdc88
出典データセット
uspto-grants-2012_11
特許番号
US08304036B2

関連ノート

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