HCID 86057409, compound → HCID 59214204, compound

HRID 1820966Notes

Reaction equation

HRID 1820966 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:11][CH:12]([CH3:17])[C:13]([F:16])([F:15])[F:14])=[C:7]([CH:10]=1)[C:8]#[N:9])=[O:2].CC(C)=[O:20].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.S(=O)(=O)(O)O.O.[O-2].[Cr+6].[O-2].[O-2]>[C:8]([C:7]1[CH:10]=[C:3]([CH:4]=[CH:5][C:6]=1[O:11][CH:12]([CH3:17])[C:13]([F:15])([F:14])[F:16])[C:1]([OH:20])=[O:2])#[N:9]

Participants

7

Reactant 2

HCID 86057409HCID 86057409, compoundHCID 131709961Jones' reagent

Product 1

HCID 59214204HCID 59214204, compound

Reagents, catalysts & solvents 4

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 440 mg (1.81 mmol) of 5-formyl-2-(2,2,2-trifluoro-1-methylethoxy)benzonitrile (from Step A) in 20 mL of acetone at 0° C. was added dropwise a solution of Jones reagent, which was prepared by dissolving 0.27 g (2.71 mmol) of chromium (VI) oxide in 0.25 mL of concentrated sulfuric acid and diluted with 2 mL of water at 0° C. The reaction mixture was gradually warmed up to rt, stirred overnight, and concentrated. The residue was diluted with 20 mL of EtOAc and washed with brine (10 mL), H2O (3×10 mL), and brine (10 mL). The organic layer was dried over MgSO4 and concentrated to give 0.44 g of the title compound: 1H NMR (500 Mhz, CDCl3) δ 1.69 (d, J=6.4, 3H), 4.94 (m, 1H), 7.16 (d, J=9.1, 1H), 8.34 (dd, J=2.0, 6.9, 1H), 8.42 (d, J=2.1, 1H).

Workup

  1. customwas prepared
  2. concentrationconcentrated
  3. additionThe residue was diluted with 20 mL of EtOAc
  4. washwashed with brine (10 mL), H2O (3×10 mL), and brine (10 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0c62fb55b57b48a4a428238a8c2d6807
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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