Tributyl(3,3-dimethylbut-1-en-1-yl)stannane → (E)-Ethyl 5-(3,3-dimethylbut-1-en-1-yl)-4-methylisoxazole-3-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Tributyl(3,3-dimethylbut-1-en-1-yl)stannane	HCID 10948728	—
Reactant	Ethyl 5-bromo-4-methyl-1,2-oxazole-3-carboxylate	HCID 58828802	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	(E)-Ethyl 5-(3,3-dimethylbut-1-en-1-yl)-4-methylisoxazole-3-carboxylate	HCID 131736501	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

(E)-Tributyl(3,3-dimethylbut-1-en-1-yl)stannane (1194 mg, 0.8 mmol) and ethyl 5-bromo-4-methylisoxazole-3-carboxylate (Intermediate A) (187 mg, 0.8 mmol) were dissolved in dioxane (6 mL) and the mixture was degassed thoroughly, refilling with nitrogen. Pd(Ph3P)4 (92 mg, 0.080 mmol) was added and the mixture was stirred at 100° C. for 16 hours. The crude reaction mixture was adsorbed onto silica and purification by chromatography eluting with 0-10% EtOAc in iso-hexane afforded the title compound;

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09403810B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-b7830f39f1214ff6b9e9ada99ad7c4ae
Source note	uspto-grants-2016_08