Sodium Carbonate → Ethyl 2-(5-methyl-2-benzofuranyl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Ethyl 2-bromobenzoate	HCID 80186	—
Reactant	1-[[3-Bromo-2-[2-[2-(triphenylmethyl)-2H-tetrazol-5-yl]phenyl]-5-benzofuranyl]methyl]-2-butyl-4-chloro-N-ethyl-1H-imidazole-5-carboxamide	HCID 54541539	—
Catalyst	HCID 178527695	HCID 178527695	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	Ethyl 2-(5-methyl-2-benzofuranyl)benzoate	HCID 18950932	313.2%

Reaction Steps

Sodium carbonate (1N; 60 ml) was added to a mixture of Intermediate 1 (4.7 g), ethyl 2-bromobenzoate (5.89 g) and tetrakis- triphenylphosphine palladium (0) (0.88 g) in DME (100 ml). The mixture was heated at reflux for 18 h, cooled to room temperature and then concentrated in vacuo. The residue was extracted with ether (3×100 ml) and the combined extracts washed with brine (1×100 ml) and dried. The solvent was evaporated to give a brown oil (5 g) which was purified by column chromatography eluting with System A (1:20) to give the title compound as a pale yellow oil (2.89 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05374646
Source dataset	uspto-grants-1994_12
ORD ID	ord-6a7887bcdc524a1d885e3ecd3d223d0c
Source note	uspto-grants-1994_12