HCID 59211734, compound → HCID 59211740, compound

HRID 1259484Notes

Reaction equation

HRID 1259484 reaction equation
[CH2:1]([CH:6]1[CH2:12][CH:11]2[CH2:13][CH:8]([CH:9]=[CH:10]2)[C:7]1=[O:14])[CH2:2][CH2:3][CH2:4][CH3:5].[H][H]>[Pd].C(O)(C)C>[CH2:1]([CH:6]1[CH2:12][CH:11]2[CH2:13][CH:8]([CH2:9][CH2:10]2)[C:7]1=[O:14])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 59211734HCID 59211734, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59211740HCID 59211740, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

3-Pentylbicyclo[3.2.1]oct-6-en-2-one (130 g, synthesized as above) was placed in a stainless steel autoclave with isopropanol (30 g) and Pd/C (1.5 g). The mixture was placed under 300 psi of hydrogen gas, and heated at 100° C. until gas uptake ceased. The resulting material was then removed from the autoclave, filtered, and distilled to yield 3-pentylbicyclo[3.2.1]octan-2-one 70 g).

Workup

  1. customThe resulting material was then removed from the autoclave
  2. filtrationfiltered
  3. distillationdistilled

Sources & evidence

ORD record
ord-a8e09e951d0a4aaca22a3afcec27fa11
Source dataset
uspto-grants-2013_06
Patent number
US08466325B2

Reaction notes

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