HCID 67918608, compound → Ethyl tricyclo[3.3.1.13,7]decane-2-propanoate

HRID 653963Notes

Reaction equation

HRID 653963 reaction equation
[CH2:1]([O:3][C:4](=[O:17])/[CH:5]=[CH:6]/[CH:7]1[CH:14]2[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:16][CH:8]1[CH2:9]3)[CH2:13]2)[CH3:2].C(OC(=O)/C=C\C1C2CC3CC(CC1C3)C2)C.[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][CH:7]1[CH:8]2[CH2:9][CH:10]3[CH2:11][CH:12]([CH2:13][CH:14]1[CH2:15]3)[CH2:16]2)[CH3:2]

Participants

6

Reactant 3

HCID 67918608HCID 67918608, compoundHCID 67918749HCID 67918749, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53933676Ethyl tricyclo[3.3.1.13,7]decane-2-propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of (E)-3-tricyclo[3.3.1.1-3,7]dec-2-yl-2-propenoic acid ethyl ester and (Z)-3-tricyclo[3.3.1.1-3,7]dec-2-yl-2-propenoic acid ethyl ester (0.018 mol, 4.23 g), dissolved in ethyl acetate (500 mL) was hydrogenated over 10% Pd/C catalyst (450 mg), (1 atm H2) with vigorous stirring until the uptake of hydrogen ceased (1 h). The reaction mixture was filtered through a pad of celite, and the filtrate dried (Na2SO4) and concentrated in vacuo to provide tricyclo[3.3.1.1-3,7]decane-2-propanoic acid ethyl ester as a colorless oil.

Workup

  1. custom(1 h)
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. dry with materialthe filtrate dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34a4a2a78e7044a994790bbbc34e32c4
Source dataset
uspto-grants-1992_07
Patent number
US05128448

Reaction notes

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