2,6-Lutidine → HCID 86716010, compound

HRID 1482497Notes

Reaction equation

HRID 1482497 reaction equation
[F:1][C:2]([C:5]1[N:10]=[CH:9][C:8]([CH:11]=C)=[CH:7][N:6]=1)([F:4])[CH3:3].N1C(C)=CC=CC=1C.C1C[O:24]CC1>O.[Os](=O)(=O)(=O)=O>[F:1][C:2]([C:5]1[N:10]=[CH:9][C:8]([CH:11]=[O:24])=[CH:7][N:6]=1)([F:4])[CH3:3]

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 8028TetrahydrofuranHCID 86716008HCID 86716008, compound

Product 1

HCID 86716010HCID 86716010, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

2-(1,1-difluoroethyl)-5-vinylpyrimidine (110 mg, 0.646 mmol) was dissolved in THF (5 ml) and water (2 ml). NaIO4 (571 mg, 2.67 mmol), 2,6-lutidine (143 mg, 0,155 ml, 1.3 mmol) and osmium tetraoxide (138 mg, 0.17 ml, 0.013 mmol, 0.078 molar in tBuOH) was added. The reaction mixture was stirred at room temperature for 2 hours. Water was added and the mixture was extracted with diethyl ether. The organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo. 1H NMR showed a mixture of aldehyde and lutidine, which was used directly in the next reaction, (166 mg, 42% yield, 28% pure). 1H NMR (CDCl3 500 MHz): δ 10.24 (s, 1H), 9.30 (s, 2H), 2.12 (t, 2H).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. additiona mixture of aldehyde and lutidine, which
  6. customwas used directly in the next reaction, (166 mg, 42% yield, 28% pure)

Sources & evidence

ORD record
ord-2c96c71f7c194fcdb76737516e22d280
Source dataset
uspto-grants-2016_08
Patent number
US09415055B2

Reaction notes

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