Ethanol → HCID 59226606, compound

HRID 1523453Notes

Reaction equation

HRID 1523453 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:15][CH:14]([C:16]([F:19])([F:18])[F:17])[CH2:13][C:12](=[O:20])[CH:11]=1)([O-:3])=[O:2].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].C(O)C.[BH4-].[Na+]>CCOC(C)=O>[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:15][C@H:14]([C:16]([F:19])([F:17])[F:18])[CH2:13][C@H:12]([OH:20])[CH:11]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 59226494HCID 59226494, compound

Product 1

HCID 59226606HCID 59226606, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-(3-Nitropyridin-4-yl)-5-(trifluoromethyl)cyclohex-2-enone (1.0 eq) was mixed with cerium(III) chloride heptahydrate (1.0 eq) and absolute ethanol (0.17) was added. The mixture was stirred at ambient temperature until all solids dissolved. the mixture was cooled on an ice bath and NaBH4 (1.2 eq) was added portion wise. The reaction was stirred on the ice bath for 1 h. The mixture was diluted with EtOAc, washed with water, dried over MgSO4, filtered and concentrated. The residue was purified by column (1:1 ethyl acetate and hexanes) to give cis-3-(3-nitropyridin-4-yl)-5-(trifluoromethyl)cyclohex-2-enol (66%). LC/MS (m/z): MH+=289.2, Rt=0.72 min.

Workup

  1. additionwas added
  2. dissolutiondissolved
  3. temperaturethe mixture was cooled on an ice bath
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column (1:1 ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-40453b82f50642fc9bcfe7668a629d88
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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