Diisopropylamine → Lithium diisopropylamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylamine	HCID 7912	—
Reactant	Trimethyltin chloride	HCID 14016	—
Reactant	4,7-Di(thiophen-2-yl)benzo(c)(1,2,5)thiadiazole	HCID 396294	—
Reactant	Butyllithium	HCID 178418339	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	Lithium diisopropylamide	HCID 2724682	—
Product	2,1,3-Benzothiadiazole, 4,7-bis(5-(trimethylstannyl)-2-thienyl)-	HCID 58153009	—

Reaction Conditions

Temperature	-78 °C

Reaction Steps

Compound (1) was dissolved in anhydrous THF (20 ml) in a nitrogen-filled flask. The solution was cooled down to −78° C. LDA was prepared from the reaction of diisopropylamine (0.5 g, 5.1 mmol, 3 eq.) and n-BuLi (3.12 ml, 5.1 mmol, 3 eq.) (1.6 M hexane solution) in anhydrous THF (2 ml), which was added to the above solution dropwise. After stirring for 1 h, trimethylstannyl chloride (3.8 ml, 3.8 mmol, 2.3 eq.) (1 M THF solution) was added and reacted for 1 h. The reaction was quenched by addition of water and the organic layer was extracted with ether, washed with water and dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, the residue was purified by recrystallization from ethanol, giving the title compound as a needle-shaped purple crystal.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09296864B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-4d36d403e34f4f5eb6ff3d944dfca4b1
Source note	uspto-grants-2016_03