N-bromobutanimide → 5-Cyclohexyl-2-methyl-furan-3-carboxylic acid ethyl ester

HRID 2236185Notes

Reaction equation

HRID 2236185 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([C:14](=[O:16])[CH3:15])=[CH:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:2].C1C(=O)N(Br)C(=O)C1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[O:16][C:14]=1[CH3:15])=[O:17])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 675368842-Acetyl-4-cyclohexyl-but-2-enoic acid ethyl ester

Product 1

HCID 675376085-Cyclohexyl-2-methyl-furan-3-carboxylic acid ethyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of 2-acetyl-4-cyclohexyl-but-2-enoic acid ethyl ester (1.79 g, 7.52 mmol) in 40 mL CCl4 was added to a slurry of NBS (1.338 g, 7.52 mmol) in 40 mL CCl4. The mixture was refluxed under argon for 12 hours, stirred at room temperature for 68 hours and then cooled in an ice bath. The precipitated solid was filtered off and the filtrate was evaporated to an oil that was purified by short-path distillation (165-185° C., 1 mm Hg) yielding 5-cyclohexyl-2-methyl-furan-3-carboxylic acid ethyl ester (1.36 g, 77%).

Workup

  1. temperatureThe mixture was refluxed under argon for 12 hours
  2. temperaturecooled in an ice bath
  3. filtrationThe precipitated solid was filtered off
  4. customthe filtrate was evaporated to an oil that
  5. distillationwas purified by short-path distillation (165-185° C., 1 mm Hg)

Sources & evidence

ORD record
ord-3ef7629acc4c49718f24229166a219d5
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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