Cyclohexane ethylacetate → HCID 58136378, compound

HRID 877217Notes

Reaction equation

HRID 877217 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:11]=[CH:12]/[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C1CCCCC1.C(OCC)(=O)C>[Pt].C(OCC)(=O)C>[NH2:8][C:7]1[C:2]([Cl:1])=[C:3]([CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 21867204Cyclohexane ethylacetateHCID 58136333HCID 58136333, compound

Product 1

HCID 58136378HCID 58136378, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

At room temperature, 50 mg of platinum on carbon (5%) were added to a solution of 200 mg (0.71 mmol) of tert-butyl(2E)-3-(2-chloro-3-nitrophenyl)prop-2-enoate in 10 ml of ethyl acetate, and the mixture was hydrogenated at atmospheric pressure for 12 hours. After the reaction had gone to completion (monitored by TLC; mobile phase cyclohexane/ethyl acetate 1:1), the reaction solution was filtered through kieselguhr and the filtrate was concentrated under reduced pressure. The crude product was purified by preparative HPLC. This gave 115 mg (0.62 mmol, 64% of theory) of the title compound.

Workup

  1. filtrationthe reaction solution was filtered through kieselguhr
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-76096ba6060f4492b54b95f17fed868a
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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