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

HRID 1376997

Reaction equation

HRID 1376997 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-1dddc5be3d3f4f748a456c8ab929c8b9
Source dataset
uspto-grants-1997_09
Patent number
US05663373

Linked notes

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