Dimethyl Sulfoxide → Ethyl 4-oxocyclohexanecarboxylate

HRID 1364304Notes

Reaction equation

HRID 1364304 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]1[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1>C(Cl)Cl>[CH2:21]([O:20][C:18]([CH:15]1[CH2:16][CH2:17][C:12](=[O:11])[CH2:13][CH2:14]1)=[O:19])[CH3:22]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 86973Ethyl 4-hydroxycyclohexanecarboxylate

Product 1

HCID 317638Ethyl 4-oxocyclohexanecarboxylateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

To a solution of oxalyl chloride (6 mL, 68.8 mmol) in DCM (100 mL) at −78° C. was added dropwise a solution of DMSO (6.4 mL, 90 mmol) in DCM (20 mL). The mixture was stirred at this temperature for 15 min before the dropwise addition of a solution of ethyl 4-hydroxycyclohexane carboxylate (4.8 mL, 30 mmol) in DCM (20 mL). The mixture was stirred at −78° C. for 3 h before addition of TEA (29.3 mL, 210 mmol) in DCM (20 mL). The mixture was then gradually warmed to rt, washed with a sat. aq. NH4Cl solution and brine, dried over MgSO4 and concentrated. The residue was purified by chromatography over SiO2 (Hex/EA 1:1) to give the title ketone (4.6 g, 90% yield) as a colourless oil.

Workup

  1. washwashed with a sat. aq. NH4Cl solution and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography over SiO2 (Hex/EA 1:1)

Sources & evidence

ORD record
ord-175a5ff60b16467aa134a105e6bee252
Source dataset
uspto-grants-2011_02
Patent number
US07888359B2

Reaction notes

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