N-methyl-2-pyrrolidone → 2-(Benzyloxy)-6-butylpyridine

HRID 495246

Reaction equation

HRID 495246 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1[CH2:21][CH2:20][CH2:19][C:18]1=O.C([Mg]Br)CCC>O1CCCC1.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:18][CH2:19][CH2:20][CH3:21])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 112644642-(Benzyloxy)-6-chloropyridineHCID 178418682HCID 178418682, compound

Product 1

HCID 666264812-(Benzyloxy)-6-butylpyridine

Reagents, catalysts & solvents 2

HCID 5483663Ferric acetylacetonateCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a flask were added 2.0 g 2-(benzyloxy)-6-chloropyridine, 5.0 ml 1-methyl-2-pyrrolidinone and 50 ml of dry tetrahydrofuran. After cooling to 5 C under nitrogen, 0.16 g iron(III) acetylacetonate were added followed by drop wise addition of 8.5 ml of a 2M solution of butylmagnesium bromide in tetrahydrofuran. After stirring for 1 hour at 22 C, the reaction was cooled to 10 C and quenched with 20 ml aqueous ammonium chloride. The mixture was diluted with water and extracted with hexane. After washing with water and removal of solvent, the product was purified by silica gel chromatography using 10% ethyl acetate in hexane to give 1.6 g of an oil.

Workup

  1. temperatureAfter cooling to 5 C under nitrogen
  2. temperaturethe reaction was cooled to 10 C
  3. customquenched with 20 ml aqueous ammonium chloride
  4. additionThe mixture was diluted with water
  5. extractionextracted with hexane
  6. washAfter washing with water and removal of solvent
  7. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ea2d5c3b88cb41308122c65766de10c0
Source dataset
uspto-grants-2009_05
Patent number
US07538931B2

Linked notes

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