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

HRID 1452382Notes

Reaction equation

HRID 1452382 reaction equation
[C:1]([O:4][C:5]1[C:6]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:7][C:8]2[O:12][C:11]([CH:13]=[CH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][C:9]=2[C:21]=1[C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:4][C:5]1[C:6]([C:26]([CH3:27])([CH3:29])[CH3:28])=[CH:7][C:8]2[O:12][C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][C:9]=2[C:21]=1[C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:3])[CH3:2]

Participants

4

Reactant 1

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

Product 1

HCID 184331765-Acetoxy-4,6-di-tert-butyl-2-octylbenzofuranYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-Acetoxy-4,6-di-tert-butyl-2-(1-octenyl)benzofuran (3.1 g) was dissolved in ethyl acetate containing 10% acetic acid (50 ml) and, after addition of 10% Pd on carbon (0.3 g), the solution was stirred under a hydrogen atmosphere for 3 h. After filtering off the Pd on carbon, the filtrate was concentrated under vacuum. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 5-acetoxy-4,6-di-tert-butyl-2-octylbenzofuran [2.95 g (yield, 96%)] as a colorless oil.

Workup

  1. filtrationAfter filtering off the Pd on carbon
  2. concentrationthe filtrate was concentrated under vacuum
  3. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-459946a79c7c4aaa8da06401b1fded53
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

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