2-Bromo-5-(methoxymethoxy)pyridine → 5-(Methoxymethoxy)-2-neopentylpyridine

HRID 20013

Reaction equation

HRID 20013 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH3:11])=[CH:4][N:3]=1.[CH2:12]([Mg]Cl)[C:13]([CH3:16])([CH3:15])[CH3:14]>C1COCC1>[CH3:11][O:10][CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 574336662-Bromo-5-(methoxymethoxy)pyridineHCID 178418809HCID 178418809, compound

Product 1

HCID 575158425-(Methoxymethoxy)-2-neopentylpyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-5-(methoxymethoxy)pyridine (30.5 g, 140 mmol) in THF (5 mL) at 0° C. under N2 is added dichloro-((bis-diphenylphosphino)ferrocenyl)-palladium(II) (4.88 g, 5.5 mmol) followed by dropwise addition of neopentylmagnesium chloride (155 mL, 155 mmol) over 2 min. After addition, the cooling bath was removed and the reaction stirred 3 h at rt. The reaction was cooled to 0° C. and saturated NH4Cl (500 mL) was added, and the aqueous layers extracted with EtOAc (3×200 mL). The combined organic layers were washed with saturated NaCl, dried (Na2SO4) and concentrated to give a red oil. Purification by vacuum filtration through a silica plug (9×7 cm, dry load, 10-20%% EtOAc/Hexanes) gives 5-(methoxymethoxy)-2-neopentylpyridine as a light yellow oil.

Workup

  1. additionAfter addition
  2. customthe cooling bath was removed
  3. temperatureThe reaction was cooled to 0° C.
  4. additionsaturated NH4Cl (500 mL) was added
  5. extractionthe aqueous layers extracted with EtOAc (3×200 mL)
  6. washThe combined organic layers were washed with saturated NaCl
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customto give a red oil
  10. customPurification
  11. filtrationby vacuum filtration through a silica plug (9×7 cm, dry load, 10-20%% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-785ced56a27f43c79815f1be393dcf7c
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Linked notes

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