Sodium Carbonate → HCID 10934165, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	6-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene	HCID 226685	—
Reactant	Potassium Acetate	HCID 517044	—
Reactant	Bis(pinacolato)diborane	HCID 2733548	—
Reactant	(2Z)-3-Iodo-2-buten-1-ol	HCID 5314691	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 10934165	HCID 10934165	77.4%

Reaction Conditions

Temperature	80 °C

Reaction Steps

Bis(pinacolato)diboron (5.8 g, 22.5 mmol), potassium acetate (4.5 g, 45 mmol) and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium (PdCl2(dppf)2) (500 mg, 0.6 mmol) were added to a solution of Intermediate 1 (4 g, 15 mmol) in 50 mL of DMF under argon. The mixture was then stirred at 80° C. for 24 h. After cooling to room temperature, 3-iodo-but-2Z-en-1-ol (6 g, 30 mmol), 2M Na2CO3 (30 ml), and PdCl2(dppf)2 (500 mg, 0.6 mmol) were added to the mixture, which was then stirred at 80° C. for another 24 h. The reaction was finally quenched with water (20 mL) and extracted with ether (3×10 mL). The organic layer was washed with brine (2×10 mL), dried (MgSO4) and concentrated to give a crude brown oil. The crude product was purified by flash chromatography using 20% EtOAc in hexane to give the title compound (3 g, 77% yield) as a colorless oil:

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06936636B2
Source dataset	uspto-grants-2005_08
ORD ID	ord-ed9cfd02c4a04a5d9c7d80ee25cdbbe0
Source note	uspto-grants-2005_08