Water → HCID 59771183, compound

HRID 408939Notes

Reaction equation

HRID 408939 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([C:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=2)[CH:10]=1)[C:5]([O:7][CH3:8])=[O:6].[NH4+].[Cl-].O>C(O)C.[Fe]>[CH3:1][O:2][C:3](=[O:24])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([C:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=2)[CH:10]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 59771162HCID 59771162, compound

Product 1

HCID 59771183HCID 59771183, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(3-cyclohex-1-enyl-4-nitro-phenyl)-malonic acid dimethyl ester (as prepared in the previous step, 200 mg, 0.600 mmol), iron powder (168 mg, 3.00 mmol) and NH4Cl (321 mg, 6.00 mmol) in 6 mL of ethanol was stirred at 80° C. for 16 h. After cooling to RT, the mixture was treated with 30 mL of H2O and extracted with EtOAc (3×20 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (30% EtOAc-hexane) to give 129 mg (71%) of the title compound as a faint yellow oil: Mass spectrum (ESI, m/z): Calcd. for C17H21NO4, 304.2 (M+H). found 304.1.

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with EtOAc (3×20 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (30% EtOAc-hexane)

Sources & evidence

ORD record
ord-030ac19822304faf83274945e961774c
Source dataset
uspto-grants-2014_06
Patent number
US08759347B2

Reaction notes

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