Cyclohexane → HCID 86670007, compound

HRID 1401127Notes

Reaction equation

HRID 1401127 reaction equation
O=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1.C1CCCCC1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15]/[C:2](/[CH2:8][CH3:9])=[CH:3]\[C:4]([O:6][CH3:7])=[O:5])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 8078CyclohexaneHCID 97314-FluoroanilineHCID 121699Methyl 3-oxovalerate

Product 1

HCID 86670007HCID 86670007, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of methyl 3-oxovalerate (10.0 g, 76.8 mmol), 4-fluoroaniline (7.36 mL, 76.8 mmol), p-toluenesulfonic acid monohydrate (730 mg, 3.84 mmol), cyclohexane (40 mL) and toluene (10 mL) was stirred with heating under reflux for 15 hr. The mixture was concentrated under reduced pressure, the insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluate, hexane:ethyl acetate=99:1→92:8) to give the title compound (11.4 g, 67%) as a yellow oil.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 15 hr
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe insoluble material was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluate, hexane:ethyl acetate=99:1→92:8)

Sources & evidence

ORD record
ord-04ef75084e364c9b8e6c173e49f86c65
Source dataset
uspto-grants-2014_12
Patent number
US08907089B2

Reaction notes

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