Triethylamine → 2-[4-(8-Hydroxy-2,2,4,4-tetramethyl-chroman-6-ylethynyl)-phenyl]-2-methyl-propionic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	6-Ethynyl-8-hydroxy-2,2,4,4-tetramethyl-chroman	HCID 21107228	—
Reactant	2-{4-[(8-Cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-phenyl}-2-methyl-propionic acid methyl ester	HCID 69077341	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Hexane	HCID 8058	—
Product	2-[4-(8-Hydroxy-2,2,4,4-tetramethyl-chroman-6-ylethynyl)-phenyl]-2-methyl-propionic acid methyl ester	HCID 69075470	—

Reaction Steps

Following General Procedure B and using 6-ethynyl-8-hydroxy-2,2,4,4-tetramethyl-chroman (Intermediate 19, 0.057 g, 0.25 mmol), methyl-2-(4-iodophenyl)-2-methyl-propionate (Reagent 2, 0.112 g, 0.37 mmol), triethyl amine (3 mL), copper(I)iodide (0.020 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.07 g, 0.1 mmol) followed by flash column chromatography over silica gel (230-400 mesh) and preparative normal phase HPLC using 5% ethyl acetate in hexane as the mobile phase, the title compound was obtained as a brown oil (0.035 g, 35%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07468391B2
Source dataset	uspto-grants-2008_12
ORD ID	ord-b79cc5aa390740d9b6a5a392b9a0a91a
Source note	uspto-grants-2008_12