Benzyl Alcohol → 2-(Benzyloxy)-6-chloro-3-nitropyridine

HRID 1862324Notes

Reaction equation

HRID 1862324 reaction equation
[H-].[Na+].Cl[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[N:5]=1.[CH2:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[Cl:13][C:6]1[N:5]=[C:4]([O:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 225652672-(Benzyloxy)-6-chloro-3-nitropyridineYield 82.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2.0 g of sodium hydride was added to a mixture of 9.65 g of 2,6-dichloro-3-nitropyridine, 5.41 g of benzyl alcohol and 30 ml of tetrahydrofuran 0° C. The mixture was stirred at 0° C. for 1.5 hours, then at room temperature for 1.5 hours. The reaction solution was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 10.93 g of 6-chloro-2-benzyloxy-3-nitropyridine.

Workup

  1. waitat room temperature for 1.5 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f4439a8240f14d2d8f47f1c20f448ba9
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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