HCID 86720197, compound → Methyl 4-acetyl-1-methylcyclohexanecarboxylate

HRID 928130Notes

Reaction equation

HRID 928130 reaction equation
Cl[C:2]([CH:4]1[CH2:9][CH2:8][C:7]([CH3:14])([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]1)=[O:3].[CH3:15][Zn]C>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:2]([CH:4]1[CH2:9][CH2:8][C:7]([CH3:14])([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:15]

Participants

6

Reactant 2

HCID 86720197HCID 86720197, compoundHCID 178477796HCID 178477796, compound

Product 1

HCID 19004752Methyl 4-acetyl-1-methylcyclohexanecarboxylate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
38 °C

Procedure

To a deoxygenated solution of methyl 4-(chlorocarbonyl)-1-methylcyclohexanecarboxylate (7.282 g, 33.3 mmol) and palladium (II) acetate (374 mg, 1.665 mmol) in 1,4-dioxane (200 mL) was added dimethylzinc (2.0 M in toluene, 16.65 mL, 33.3 mmol). The black reaction mixture was heated under an inert atmosphere at 38° C. for 15 hours before being diluted with water (30 mL). The resulting suspension was filtered twice through CELITE. The filtrate was dried over magnesium sulfate and concentrated under reduced pressure. The resiude was purified by chromatography on silica gel (5-45% ethyl acetate/hexanes) to afford methyl 4-acetyl-1-methylcyclohexanecarboxylate. MS ESI calc'd. for C11H18O3 [M+H]+ 199. found 199.

Workup

  1. customThe black reaction mixture
  2. filtrationThe resulting suspension was filtered twice through CELITE
  3. dry with materialThe filtrate was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resiude was purified by chromatography on silica gel (5-45% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-e53f08950e404ee6979d86e3da9d7c73
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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