Water → HCID 18800652, compound

HRID 849051Notes

Reaction equation

HRID 849051 reaction equation
[C:1]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12])([O:3][CH2:4][CH3:5])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH:21]1[CH2:25][CH2:24][CH2:23][O:22]1.O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[O:22]1[CH2:23][CH2:24][CH2:25][CH:21]1[CH2:20][C:6]1([C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 95543Ethyl 2-oxocyclohexanecarboxylate

Product 1

HCID 18800652HCID 18800652, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

2-carboethoxycyclohexanone (1 mmol), finely powdered potassium carbonate (2 mmol), 2-bromomethyltetrahydrofuran (1.5 mmol), and tetrabutylammonium iodide (10 mg/mmol) are combined in dry DMF (1.25 mL/mmol) and stirred under N2 at 55 to 60° C. for 16 to 18 hours. The room temperature reaction mixture is poured into water and extracted with Et2O and EtOAc. The combined organics are washed with brine, dried, and stripped of all solvent under reduced pressure to provide 2-tetrahydrofuranylmethyl-2-carboethoxycyclohexanone. This material is combined with lithium chloride (5 mmol), water (1.05 mmol) and dimethyl sulfoxide (5 mL/mmol) and the mixture refluxed for approximately 4 hrs. The mixture is poured into water and extracted with Et2O and EtOAc. The combined organics are washed with brine, dried, and stripped of all solvent under reduced pressure to generate the title material.

Workup

  1. customThe room temperature reaction mixture
  2. extractionextracted with Et2O and EtOAc
  3. washThe combined organics are washed with brine
  4. customdried

Sources & evidence

ORD record
ord-41c840fc611b48e19969a80699c5c036
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

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