Water → [5-(tert-Butyldimethylsilyloxymethyl)pyridin-2-yl]tri-n-butylstannane

HRID 1440460Notes

Reaction equation

HRID 1440460 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[CH:4][N:3]=1.[Li]CCCC.[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25].O>C1COCC1>[Si:10]([O:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Sn:26]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:22][CH2:23][CH2:24][CH3:25])=[N:3][CH:4]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 15096Tributyltin ChlorideHCID 6425754Pyridine, 2-bromo-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-HCID 178418339Butyllithium

Product 1

HCID 11756135[5-(tert-Butyldimethylsilyloxymethyl)pyridin-2-yl]tri-n-butylstannaneYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled (-78° C.), stirred solution of 2-bromo-5-(tert-butyldimethylsilyloxy)methylpyridine (6.8 g, 0.022 mol) in THF (60 mL) was added 1.6M nBuLi in hexanes (14.1 mL, 0.22 mol). After 1 h, tri-n-butyltin chloride (6.1 mL, 0.022 mol) was added and stirring was continued for 3 h. Water was added, and the mixture was warmed to room temperature and extracted with ether. The combined extracts were dried (MgSO4) and concentrated to give 11.5 g (100%) of product as a brown oil.

Workup

  1. waitwas continued for 3 h
  2. temperaturethe mixture was warmed to room temperature
  3. extractionextracted with ether
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bcd7b649426f4c7882feb9c88915ce6a
Source dataset
uspto-grants-1996_03
Patent number
US05498776

Reaction notes

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