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

HRID 1900494Notes

Reaction equation

HRID 1900494 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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%)]. Mass 392(M+), 301, 277, 167, 91, 57

Workup

  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)

Sources & evidence

ORD record
ord-7c9aa8efb3b549cca873fb7a705ec02c
Source dataset
uspto-grants-1996_11
Patent number
US05574178

Reaction notes

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