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

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Tributyltin Chloride	HCID 15096	—
Reactant	Pyridine, 2-bromo-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-	HCID 6425754	—
Reactant	Butyllithium	HCID 178418339	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	[5-(tert-Butyldimethylsilyloxymethyl)pyridin-2-yl]tri-n-butylstannane	HCID 11756135	102%

Reaction Conditions

Temperature	-78 °C

Reaction Steps

To a cooled (-78° C.), stirred solution of 2-bromo-5-(tert-butyldimethylsiloxy)methylpyridine (6.8 g, 0.022 mol) in THF (60 mL) was added 1.6M nBuLi in hexanes (14.1 mL, 0.022 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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05149699
Source dataset	uspto-grants-1992_09
ORD ID	ord-c2c8f899b9c14a66a28b3eecbf529c77
Source note	uspto-grants-1992_09