Sodium hydride → Pyridin-2-yl 1,1,1-trifluoro-2-methylpropan-2-yl carbonate

HRID 2361595Notes

Reaction equation

HRID 2361595 reaction equation
[H-].[Na+].[F:3][C:4]([F:10])([F:9])[C:5]([CH3:8])([OH:7])[CH3:6].[C:11](=O)([O:19]C1C=CC=CN=1)[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1>C1COCC1>[C:11](=[O:19])([O:7][C:5]([CH3:8])([CH3:6])[C:4]([F:10])([F:9])[F:3])[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 681821,1,1-Trifluoro-2-methylpropan-2-olHCID 2757370Carbonic acid di-2-pyridyl ester

Product 1

HCID 23595245Pyridin-2-yl 1,1,1-trifluoro-2-methylpropan-2-yl carbonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a slurry of NaH (1.03 g, 25.8 mmol) in THF (70 mL) was added 1,1,1-trifluoro-2-methylpropan-2-ol (3 g, 23.42 mmol). The reaction was stirred at 0° C. for 20 min. A solution of dipyridin-2-yl carbonate (5.06 g, 23.42 mmol) in THF (30 mL) was then added to the mixture. The resulting solution was stirred at room temperature for overnight. Filtered the resulting solid byproducts and washed with EtOAc (2×20 mL). The combined organic layers was washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resulting white pyridin-2-yl (1,1,1-trifluoro-2-methylpropan-2-yl) carbonate (1.24 g, 21%) was directly used as a reagent.

Workup

  1. stirringThe resulting solution was stirred at room temperature for overnight
  2. filtrationFiltered the resulting solid byproducts
  3. washwashed with EtOAc (2×20 mL)
  4. washThe combined organic layers was washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3094bdbc8572411eacf19389889fd07d
Source dataset
uspto-grants-2014_04
Patent number
US08691757B2

Reaction notes

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