HCID 58136329, compound → HCID 58136335, compound

HRID 626412Notes

Reaction equation

HRID 626412 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:4][C:3]=1[N+:17]([O-])=O>C1COCC1.C(O)C.[Pd]>[NH2:17][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 1

HCID 58136329HCID 58136329, compound

Product 1

HCID 58136335HCID 58136335, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 81.0 g (303 mmol) of tert-butyl (2E)-3-(4-fluoro-3-nitrophenyl)acrylate in a mixture of 810 ml of THF and 810 ml of ethanol was inertized with argon, and 8.1 g of 10% palladium on carbon were added. The suspension was stirred at RT under a hydrogen atmosphere at standard pressure for 9 h. The reaction mixture was then filtered off with suction through kieselguhr, and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (mobile phase petroleum ether/ethyl acetate 4:1). This gave 66.0 g (91% of theory) of the title compound.

Workup

  1. additionwere added
  2. filtrationThe reaction mixture was then filtered off with suction through kieselguhr
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by chromatography on silica gel (mobile phase petroleum ether/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-9151da9ce3ea48678ac14a22a2324b5f
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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