Ethyl 4-oxocyclohexanecarboxylate → HCID 69234116, compound

HRID 1593650Notes

Reaction equation

HRID 1593650 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl.[F:14][C:15]([F:26])([F:25])[O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23]N)=[CH:19][CH:18]=1>C(O)C>[F:14][C:15]([F:25])([F:26])[O:16][C:17]1[CH:22]=[C:21]2[C:20](=[CH:19][CH:18]=1)[NH:23][C:9]1[CH2:10][CH2:11][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][C:8]2=1

Participants

4

Reactant 2

HCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 27773284-(Trifluoromethoxy)phenylhydrazine hydrochloride

Product 1

HCID 69234116HCID 69234116, compoundYield 147.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-oxocyclohexane carboxylic acid ethyl ester (3.75 g, 0.022 mol), 4-trifluoromethoxy phenylhydrazine hydrochloride (5 g, 0.0218 mol) and anhydrous ethanol (68 mL) was refluxed overnight under nitrogen. The solvent was evaporated and the residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic extracts were washed with 1:1 water/brine and dried over anhydrous magnesium sulfate. Removal of the solvent provided a yellow solid that was dried in vacuo (7.15 g). The material from two runs (11.64 g) was chromatographed on silica gel Merck 60 using a 5 to 15% gradient of ethyl acetate in hexane to yield the title compound as a pale tan solid (10.54 g, 92%), m.p. 131-132° C. MS [(+)ES, m/z}: 328.1 [M+H]+. MS [(−)ES, m/z]: 326.1 {M−H]−. HPLC: Chromolith Monolith column, 0.46×10 cm, gradient of acetonitrile in water (0.01% TFA), 4 mL/min, detection at 280 nm; Rt 2.45 min.

Workup

  1. temperaturewas refluxed overnight under nitrogen
  2. customThe solvent was evaporated
  3. customthe residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  4. washThe organic extracts were washed with 1:1 water/brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customRemoval of the solvent
  7. customprovided a yellow solid
  8. customthat was dried in vacuo (7.15 g)
  9. customThe material from two runs (11.64 g) was chromatographed on silica gel Merck 60 using a 5 to 15% gradient of ethyl acetate in hexane

Sources & evidence

ORD record
ord-60eb753284e24a4d91366d40d61f0f89
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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