Ethanol → HCID 90417610, compound

HRID 576169Notes

Reaction equation

HRID 576169 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([N+:12]([O-:14])=[O:13])=[CH:4][N:3]=1.[CH2:15]([OH:17])[CH3:16].[H-].[Na+].O>C1COCC1>[CH2:15]([O:17][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([N+:12]([O-:14])=[O:13])=[CH:4][N:3]=1)[CH3:16]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 24758Sodium hydrideHCID 38491402-Chloro-5-nitro-3-(trifluoromethyl)pyridine

Product 1

HCID 90417610HCID 90417610, compoundYield 20.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-chloro-5-nitro-3-(trifluoromethyl)pyridine (500 mg, 2.207 mmol) in THF (10 mL) was added ethanol (0.155 mL, 2.65 mmol) and NaH (132 mg, 3.31 mmol). Then the mixture was stirred at 0° C. for 30 min, then warmed to rt and stirred for 16 h. The mixture was added to H2O and extracted with EA (2×50 mL) to give the organic layer. The combined organic extract was washed with brine, dried over Na2SO4 and concentrated to yield a brown oil of 2-ethoxy-5-nitro-3-(trifluoromethyl)pyridine (120 mg, 0.457 mmol, 20.7% yield): 1H NMR (400 MHz, CD3OD) δ 9.27 (d, J=2.5 Hz, 1H), 8.75 (d, J=2.5 Hz, 1H), 4.67 (m, 2H), 1.47 (t, J=7.0 Hz, 3H).

Workup

  1. temperaturewarmed to rt
  2. stirringstirred for 16 h
  3. extractionextracted with EA (2×50 mL)
  4. customto give the organic layer
  5. extractionThe combined organic extract
  6. washwas washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d4707eec1f1843068acd5547d25fedcb
Source dataset
uspto-grants-2015_05
Patent number
US09035063B2

Reaction notes

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