Pentane → 5-Benzyloxy-4-t-butyl-2-(1-octenyl)benzofuran

HRID 1376967

反応式

HRID 1376967 の反応式
CCCCC.C([Li])CCC.[Br-].[CH2:12]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:38]([O:45][C:46]1[CH:47]=[CH:48][C:49]2[O:53][C:52]([CH:54]=O)=[CH:51][C:50]=2[C:56]=1[C:57]([CH3:60])([CH3:59])[CH3:58])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>O1CCCC1>[CH2:38]([O:45][C:46]1[CH:47]=[CH:48][C:49]2[O:53][C:52]([CH:54]=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:51][C:50]=2[C:56]=1[C:57]([CH3:58])([CH3:60])[CH3:59])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

参加物

6

反応物 4

HCID 8003PentaneHCID 2724567Heptyltriphenylphosphonium bromideHCID 234428795-Benzyloxy-4-t-butyl-2-formylbenzofuranHCID 178418339Butyllithium

生成物 1

HCID 543087225-Benzyloxy-4-t-butyl-2-(1-octenyl)benzofuran収率 91.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A pentane solution (2.6 ml, 4.2 mmol) of 1.6M n-butyllithium was added dropwise to a solution of n-heptyltriphenylphosphonium bromide (1.84 g, 4.2 mmol) in tetrahydrofuran (10 ml) under a nitrogen atmosphere. After stirring the mixture at room temperature for 30 min, a solution of 5-benzyloxy-4-tert-butyl-2-formylbenzofuran (1.0 g, 3.2 mmol) in tetrahydrofuran (10 ml) was added dropwise. Subsequently, the mixture was stirred at room temperature for 30 min, poured into ice water and subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and water, then dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica Gel chromatography (chloroform) to afford 5-benzyloxy-4-tert-butyl-2-(1-octenyl)benzofuran [1.14 g (yield, 91%)].

後処理

  1. stirringSubsequently, the mixture was stirred at room temperature for 30 min
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica Gel chromatography (chloroform)

出典と根拠

ORDレコード
ord-8f9839940081438eb9ea5381c16840c8
出典データセット
uspto-grants-1997_09
特許番号
US05663373

関連ノート

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