2‐tert‐Butyl‐5‐methyl‐2‐propyl‐5H‐furan → HCID 11658402, compound

HRID 1867216Notes

Reaction equation

HRID 1867216 reaction equation
[C:1]([C:5]1([CH2:11][CH2:12][CH3:13])[CH:9]=[CH:8][CH:7]([CH3:10])[O:6]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CCOCC>[C:1]([C:5]1([CH2:11][CH2:12][CH3:13])[CH2:9][CH2:8][CH:7]([CH3:10])[O:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 116583972‐tert‐Butyl‐5‐methyl‐2‐propyl‐5H‐furanHCID 178418361HCID 178418361, compound

Product 1

HCID 11658402HCID 11658402, compoundYield 126.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

At ambient temp., a suspension of 2.91 g (10.4 mmol) of 2-tert-butyl-5-methyl-2-propyl-2,5-dihydrofuran and 1.06 g (1.00 mmol) of 10% palladium on activated charcoal in 60 mL of dry ether was hydrogenated for 4 h in a Parr apparatus at 2.5 bar hydrogen pressure. The catalyst was filtered off over a pad of Celite, and the solvent evaporated. The resulting residue was distilled in a Kugelrohr apparatus to provide at 75-85° C./20 mbar 2.43 g (80%) of the title compound as a colorless odoriferous liquid.

Workup

  1. filtrationThe catalyst was filtered off over a pad of Celite
  2. customthe solvent evaporated
  3. distillationThe resulting residue was distilled in a Kugelrohr apparatus

Sources & evidence

ORD record
ord-9fed2e1ba54c4d96896cde0c0ef59aa6
Source dataset
uspto-grants-2009_12
Patent number
US07632790B2

Reaction notes

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