Water → Ethyl(6-(((trifluoromethyl)sulfonyl)oxy)-1-benzothiophen-3-yl)acetate

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Trifluoromethanesulfonic anhydride	HCID 67749	—
Reactant	(6-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester	HCID 57431998	—
Solvent	Acetonitrile	HCID 6342	—
Product	Ethyl(6-(((trifluoromethyl)sulfonyl)oxy)-1-benzothiophen-3-yl)acetate	HCID 57443344	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a solution of ethyl(6-hydroxy-1-benzothiophen-3-yl)acetate (500 mg) and triethylamine (0.592 mL) in CH3CN (20 mL) was added Tf2O (0.417 mL). The mixture was stirred at 0° C. for 10 min. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with 1N HCl and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (745 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09238639B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-99f88f73cddc45bbbfdbc950a2b3a946
Source note	uspto-grants-2016_01