Methanol → Methyl 3-oxocyclohexane-1-carboxylate

HRID 521177Notes

Reaction equation

HRID 521177 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([OH:10])=[O:9])[CH2:3]1.[Si](C=[N+]=[N-])(C)(C)[CH3:12].CO>C(OCC)C>[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH3:12])=[O:9])[CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 27602523-Oxocyclohexane-1-carboxylic acid

Product 1

HCID 566099Methyl 3-oxocyclohexane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-oxocyclohexanecarboxylic acid (1.0 g, 7.0 mmol) in diethyl ether (28 mL) was added dropwise TMS-diazomethane (3.5 mL, 7.0 mmol, 2.0 mL in diethyl ether). MeOH (30 mL) was added and the mixture was maintained at ambient temperature for 30 minutes. The mixture was concentrated in vacuo, and the residue was purified by MPLC on silica gel (using a gradient elution of 0-45% EtOAc/hexanes). Desired fractions were identified, combined, and concentrated in vacuo to afford the title compound.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by MPLC on silica gel (
  3. washa gradient elution of 0-45% EtOAc/hexanes)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-331e63e2801142b8af421c08c9574e82
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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