Ammonium Chloride → 5-Acetoxy-4,6-di-tert-butyl-2-(1-octenyl)benzofuran

HRID 1900524ノート

反応式

HRID 1900524 の反応式
C([Li])CCC.[Br-].[CH2:7]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[C:33]([O:36][C:37]1[C:38]([C:52]([CH3:55])([CH3:54])[CH3:53])=[CH:39][C:40]2[O:44][C:43]([CH:45]=O)=[CH:42][C:41]=2[C:47]=1[C:48]([CH3:51])([CH3:50])[CH3:49])(=[O:35])[CH3:34].[Cl-].[NH4+]>O1CCCC1.CCCCC>[C:33]([O:36][C:37]1[C:38]([C:52]([CH3:54])([CH3:53])[CH3:55])=[CH:39][C:40]2[O:44][C:43]([CH:45]=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:42][C:41]=2[C:47]=1[C:48]([CH3:49])([CH3:50])[CH3:51])(=[O:35])[CH3:34]

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 2724567Heptyltriphenylphosphonium bromideHCID 229186695-Acetoxy-4,6-di-tert-butyl-2-formylbenzofuranHCID 178418339Butyllithium

生成物 1

HCID 537687215-Acetoxy-4,6-di-tert-butyl-2-(1-octenyl)benzofuran収率 97%

試薬・触媒・溶媒 2

HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A pentane solution (6.0 ml) of 1.6M n-butyllithium was added dropwise to a solution of n-heptyltriphenylphosphonium bromide (4.2 g) in tetrahydrofuran (30 ml) under a nitrogen atmosphere. After stirring the mixture at room temperature for 90 min, a solution of 5-acetoxy-4,6-di-tert-butyl-2-formylbenzofuran (2.54 g) in tetrahydrofuran (20 ml) was added dropwise. Subsequently, the mixture was heated under reflux for 1 h and, after cooling, a saturated aqueous solution of ammonium chloride was added and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 5-acetoxy-4,6-di-tert-butyl-2-(1-octenyl)benzofuran [3.1 g (yield, 97%)] as a colorless oil.

後処理

  1. temperatureSubsequently, the mixture was heated
  2. temperatureunder reflux for 1 h
  3. temperatureafter cooling
  4. extractionthe mixture was subjected to extraction with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

出典と根拠

ORDレコード
ord-6caa1f97d57148d39032603748e39bcd
出典データセット
uspto-grants-1996_11
特許番号
US05574178

反応ノート

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