Indole → Methyl 3-(1H-indol-1-yl)propanoate

Participants

Role	Name	HCID	Charge
Reactant	Indole	HCID 798	—
Reactant	Methyl Acrylate	HCID 7294	—
Reactant	1,8-Diazabicyclo(5.4.0)undec-7-ene	HCID 81184	—
Solvent	Acetonitrile	HCID 6342	—
Product	Methyl 3-(1H-indol-1-yl)propanoate	HCID 5150745	43.3%

Reaction Conditions

Temperature	50 °C

Reaction Steps

To the solution of indole (1.20 g, 10.24 mmol) and methyl acrylate (1.384 mL, 15.37 mmol) in MeCN (20 mL) was added DBU (0.772 mL, 5.12 mmol). The mixture was heated at 50° C. overnight. Purification via flash chromatography then afforded the title compound (1.0 g, 4.43 mmol, 90% purity, 43.2% yield). LCMS: rt=3.04 min, [M+H+]=204

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08637536B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-5809aec56ec54ed1bb4c66a95ca98280
Source note	uspto-grants-2014_01