Hexane → 5-Phenylpent-4-enyl-1-ol

HRID 477010

反応式

HRID 477010 の反応式
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:7]([Li])[CH2:8][CH2:9][CH3:10].[OH:12][CH:13]1CCCO1>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:3]1(/[CH:10]=[CH:9]/[CH2:8][CH2:7][CH2:13][OH:12])[CH:2]=[CH:1][CH:6]=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 8058HexaneHCID 93002Tetrahydro-2-hydroxyfuranHCID 178418339Butyllithium

生成物 1

HCID 53716955-Phenylpent-4-enyl-1-ol

試薬・触媒・溶媒 2

HCID 70671Benzyltriphenylphosphonium chloride触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 4 g of benzyltriphenylphosphonium chloride in 20 ml of tetrahydrofuran was added 7.07 ml of 1.6M hexane solution of n-butyl lithium under cooling at 0° C. After stirring at room temperature for 30 minutes, 1 g of 2-hydroxytetrahydrofuran was added, followed by stirring at room temperature for 16 hours. Subsequently, after refluxing for 2 hours, insolubles were filtered off and the solvent was distilled off. The residue was purified by silica gel column chromatography (solvent: hexane-ethyl acetate=2:1) to give 2 g of (E)-5-phenyl-4-penten-1-ol as a colorless oily substance.

後処理

  1. stirringby stirring at room temperature for 16 hours
  2. temperatureSubsequently, after refluxing for 2 hours
  3. filtrationinsolubles were filtered off
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by silica gel column chromatography (solvent: hexane-ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-021a769ec5bf44a297e6ddea2e4655b7
出典データセット
uspto-grants-1989_12
特許番号
US04886817

関連ノート

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