Methanol → Ethyl 6-methoxybenzofuran-2-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	1,8-Diazabicyclo(5.4.0)undec-7-ene	HCID 81184	—
Reactant	Ethyl 2-(2-formyl-5-methoxyphenoxy)acetate	HCID 21476959	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	Ethyl 6-methoxybenzofuran-2-carboxylate	HCID 11830962	93.9%

Reaction Conditions

Temperature	160 °C

Reaction Steps

A mixture of the product of Step A (1.28 g, 5.37 mmol) and DBU (0.3 ml) was heated for 3 h at 160° C. with stirring, cooled to room temperature and dissolved in EtOAc:MeOH mixture (99:1). The mixture was filtered through the silica bead and the filtrate was evaporated to give the title compound (1.11 g; 77%), as colourless solid. 1H-NMR (CDCl3) 1.40 (tr, 3H, J=7.13 Hz); 3.85 (s, 3H); 4.40 (q, 2H, J=7.13, 14.25 Hz); 4.45 (s, 1H); 6.91 (dd, 1H, J=2.25, 8.68 Hz); 7.04 (d, 1H, J=1.87 Hz); 7.51 (d, 1H, J=5.17 Hz),

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181182B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-5a541607e3a34924aa9296a3ce7298a1
Source note	uspto-grants-2015_11