Реакция #48291

Уравнение реакции

neopentylmagnesium chloride

2-bromo-5-(methoxymethoxy)pyridine

→

5-(methoxymethoxy)-2-neopentylpyridine

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONAfter addition
2. 2
   Другоеthe cooling bath was removed
3. 3
   ТемператураThe reaction was cooled to 0° C.
4. 4
   workup.ADDITIONsaturated NH4Cl (500 mL) was added
5. 5
   Экстракцияthe aqueous layers extracted with EtOAc (3×200 mL)
6. 6
   ПромывкаThe combined organic layers were washed with saturated NaCl
7. 7
   Сушкаdried (Na2SO4)
8. 8
   Концентрированиеconcentrated
9. 9
   Другоеto give a red oil
10. 10
    ДругоеPurification
11. 11
    Фильтрацияby vacuum filtration through a silica plug (9×7 cm, dry load, 10-20%% EtOAc/Hexanes)

Методика

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.

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