Diethyl 4,4-difluoroheptanedioate → Ethyl 5,5-difluoro-2-oxocyclohexane-1-carboxylate

HRID 2045109Notes

Reaction equation

HRID 2045109 reaction equation
[F:1][C:2]([F:17])([CH2:10][CH2:11][C:12]([O:14]CC)=O)[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1>[F:17][C:2]1([F:1])[CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:12](=[O:14])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 10264195Diethyl 4,4-difluoroheptanedioateHCID 23665647Potassium tert-butoxide

Product 1

HCID 53362434Ethyl 5,5-difluoro-2-oxocyclohexane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of diethyl 4,4-difluoroheptanedioate (4.3 g) in toluene (50 mL) was added potassium 2-methylpropan-2-olate (2.87 g) and the reaction stirred overnight at room temperature. The reaction was quenched with 1N aqueous HCl (100 mL) and extracted with diethyl ether (150 mL). The ether layer was washed with brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 40 g) eluting with a gradient of 1% to 5% ethyl acetate/hexanes gave the title compound.

Workup

  1. customThe reaction was quenched with 1N aqueous HCl (100 mL)
  2. extractionextracted with diethyl ether (150 mL)
  3. washThe ether layer was washed with brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washSilica gel chromatography (Reveleris 40 g) eluting with a gradient of 1% to 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-61725950fcc24c349a3a0ad3f6feb947
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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