Methanol → Methyl 5-cyano-5-(2-fluorophenyl)-2-oxocyclohexanecarboxylate

HRID 617741Notes

Reaction equation

HRID 617741 reaction equation
[C:1]([C:3]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])([CH2:10][CH2:11][C:12]([O:14]C)=O)[CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])#[N:2].[H-].[Na+].CO>C1(C)C=CC=CC=1>[C:1]([C:3]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[CH2:4][CH:5]([C:6]([O:8][CH3:9])=[O:7])[C:12](=[O:14])[CH2:11][CH2:10]1)#[N:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 21834548Dimethyl 4-cyano-4-(2-fluorophenyl)heptanedioate

Product 1

HCID 21834546Methyl 5-cyano-5-(2-fluorophenyl)-2-oxocyclohexanecarboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dimethyl 4-cyano-4-(2-fluorophenyl)heptanedioate (D18, 35.86 g, 0.12 mol) was stirred under Ar in toluene (500 ml) as sodium hydride (80% in mineral oil, 3.5 g, 0.12 mol) was added. Methanol (10 ml) was added dropwise, and the mixture was then stirred at reflux for 16 h, partitioned between ethyl acetate and dilute HCl, and separated. The organic portion was washed with brine, dried (Na2SO4) and evaporated to an oil. This was dissolved in dichloromethane (500 ml), filtered, and evaporated to give the title compound (30.66 g, 95%) as a cream solid.

Workup

  1. additionwas added
  2. temperatureat reflux for 16 h
  3. custompartitioned between ethyl acetate and dilute HCl
  4. customseparated
  5. washThe organic portion was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated to an oil
  8. dissolutionThis was dissolved in dichloromethane (500 ml)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-4959630818e84134a1141e0a540952cc
Source dataset
uspto-grants-1999_09
Patent number
US05952325

Reaction notes

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