Chlorotrimethylsilane → 2-Trimethylsilyloxy-4-(4-(methylthio)phenyl)-3,4-dihydrofuran

Participants

Role	Name	HCID	Charge
Reactant	Chlorotrimethylsilane	HCID 6397	—
Reactant	Pentane	HCID 8003	—
Reactant	2(5H)-Furanone	HCID 10341	—
Reactant	4-Bromothioanisole	HCID 66037	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	HCID 178418306	HCID 178418306	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Diethyl Ether	HCID 3283	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Triethylamine	HCID 8471	—
Product	2-Trimethylsilyloxy-4-(4-(methylthio)phenyl)-3,4-dihydrofuran	HCID 18400192	—

Reaction Conditions

Temperature	-78 °C

Reaction Steps

To a solution of 3.86 g (19 mmol) of 4-bromothioanisole in 90 mL of Et2O cooled at -78° C., is added 22 mL of 1.7M solution of t-BuLi in pentane (38 mmol) dropwise. The reaction mixture is stirred for 15 min at -78° C. and 3.8 g of CuI is added and the reaction mixture is allowed to warm to -40° C. over a period of 30 min. A solution of 1.7 g of 2(5H)-furanone in 10 mL of THF is added. After stirring for 1 h, 2 mL of freshly distilled TMSCl is added dropwise. The reaction mixture is then treated with 2 mL of Et3N and 50 mL of sat. NaHCO3, and extracted with 100 mL of Et2O. The Et2O layer is dried over Na2SO4 and concentrated to give the crude title compound which is used for the next step without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05663195
Source dataset	uspto-grants-1997_09
ORD ID	ord-dc44e7dca3934c94a0f35f803c14ead5
Source note	uspto-grants-1997_09