HCID 10900116, compound → HCID 54503490, compound

HRID 1862583Notes

Reaction equation

HRID 1862583 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH2:7][C:8]1([C:14]#[N:15])[CH:13]=[CH:12][CH2:11][CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2]>O.CO.[Pd]>[C:1]([O:5][C:6](=[O:16])[CH2:7][C:8]1([C:14]#[N:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 10900116HCID 10900116, compound

Product 1

HCID 54503490HCID 54503490, compoundYield 56.5%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Added 5% Pd/C, 50% H2O catalyst (94.0 mg, 22.1 μmol) to a solution of (1-cyanocyclohexa-2,5-dienyl)acetic acid t-butyl ester (0.50 g, 2.3 mmol) in MeOH (10 mL). After shaking the reaction mixture under 20 psi H2 at room temperature for 18.5 hours, the pressure was slowly released. The reaction was filtered and concentrated under reduced pressure. Flash chromatography (SiO2, 1:3 hexane:CH2Cl2-100% CH2Cl2) afforded 0.29 g (56%) of product as an oil.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db2299b5fe234815844eaae63569d235
Source dataset
uspto-grants-2003_03
Patent number
US06538148B2

Reaction notes

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