Benzyl Alcohol → Ammonia

HRID 1416629Notes

Reaction equation

HRID 1416629 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[H-].[Na+].[CH2:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[CH2:14]([O:21][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH3:4]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 27366983-Chloro-5-(trifluoromethyl)pyridine

Product 2

HCID 222AmmoniaHCID 218518253-Benzyloxy-5-(Trifluoromethyl)Pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a 3.63 g (20 mmol) sample of 3-chloro-5-trifluoromethylpyridine dissolved in 15 mL of DMF and cooled to 0° C. was added 960 mg of NaH (60%), 2.07 mL of benzyl alcohol was added slowly. The reaction mixture was stirred for 2 hours at 40° C. The solvent was then evaporated in vacuo and the mixture diluted with chloroform, washed with saturated NaHCO3 and a brine solution. The organic layer was then dried over MgSO4. The resulting crude material was purified by flash chromatography on silica gel to give the title product MS (DCI/NH3) m/e 154(M+H)+. 1HNMR (CDCl3, 300 MHz) δ: 8.56 (d, J=1.8 Hz, 1H), 8.47 (d, J=0.9 Hz, 1H), 7.51 (dd, J=1, 0.9 Hz, 1H).

Workup

  1. additionwas added slowly
  2. customThe solvent was then evaporated in vacuo
  3. additionthe mixture diluted with chloroform
  4. washwashed with saturated NaHCO3
  5. dry with materialThe organic layer was then dried over MgSO4
  6. customThe resulting crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e10fb7f08cb74e499ebae0d6d934d6f4
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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