HCID 123543803, compound → HCID 89750507, compound

HRID 1468252Notes

Reaction equation

HRID 1468252 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH:8]=[C:9]([CH3:14])[CH2:10][CH2:11][CH:12]=[O:13]>C(OCC)(=O)C.[Pd]>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][CH:9]([CH3:14])[CH2:10][CH2:11][CH:12]=[O:13]

Participants

4

Reactant 1

HCID 123543803HCID 123543803, compound

Product 1

HCID 89750507HCID 89750507, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-(Bicyclo[2.2.1]heptan-2-yl)-4-methylpent-4-enal (20.6 g; 107 mmol) was hydrogenated in ethyl acetate (70 ml) in the presence of 5% palladium on charcoal (1.4 g) at room temperature and 30 bars. The product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 9:1) followed by bulb-t-bulb distillation (100° C./0.25 mbar). The product was obtained as a 1:1 mixture of diastereoisomers in 65% yield.

Workup

  1. customThe product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 9:1)
  2. distillationfollowed by bulb-t-bulb distillation (100° C./0.25 mbar)
  3. customThe product was obtained as a 1:1 mixture of diastereoisomers in 65% yield

Sources & evidence

ORD record
ord-02b44614a2f74706aaff2c58b41a3a4b
Source dataset
uspto-grants-2015_04
Patent number
US09000226B2

Reaction notes

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