Benzyl Alcohol → HCID 22504065, compound

HRID 1814317Notes

Reaction equation

HRID 1814317 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([OH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([O:25][CH3:26])[N:17]=1>C1COCC1.O.[OH-].[Na+]>[CH2:7]([O:14][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([O:25][CH3:26])[N:17]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 244Benzyl AlcoholHCID 27950292-Chloro-6-methoxy-3-nitropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 22504065HCID 22504065, compoundYield 49.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Potassium tert-butoxide (4.28 g, 38.2 mmol) was added to a solution of benzyl alcohol (3.29 mL, 31.8 mmol) in 66 mL anhydrous THF. The mixture was stirred at room temperature for 20 minutes. 2-Chloro-6-methoxy-3-nitropyridine (5.00 g, 26.5 mmol) was added and the reaction was stirred at vigorous reflux for 18 h. TLC analysis (silica, 1:1 CH2Cl2-hexanes) indicated no unreacted starting material. The reaction mix was diluted with 200 mL H2O and 20 mL 10% aqueous NaOH. The dilution was extracted with ethyl acetate (75 mL) and then with CH2Cl2 (50 mL). The organic extractions were combined, washed with brine (100 mL), dried over Na2SO4, filtered through celite, and concentrated. The crude product was purified by flash chromatography (SiO2, 1:1.5 CH2Cl2-hexanes) to give 3.41 g (13.1 mmol, 49%) of 2-benzyloxy-6-methoxy-3 nitro-pyridine. MS (APCI) m/z 261.1 (M+1).

Workup

  1. stirringthe reaction was stirred
  2. temperatureat vigorous reflux for 18 h
  3. additionThe reaction mix
  4. extractionThe dilution was extracted with ethyl acetate (75 mL)
  5. extractionThe organic extractions
  6. washwashed with brine (100 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered through celite
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography (SiO2, 1:1.5 CH2Cl2-hexanes)

Sources & evidence

ORD record
ord-c8566fbcacc24216934d5ee309340af0
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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