Tetrahydrofuran → [4-(2,2,4,4-Tetramethyl-chroman-6-yl-ethynyl)phenyl]acetic Acid Methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Methyl 4-Iodophenylacetate	HCID 10378700	—
Reactant	2,2,4,4-Tetramethyl-6-ethynylchroman	HCID 15661138	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Hexane	HCID 8058	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	[4-(2,2,4,4-Tetramethyl-chroman-6-yl-ethynyl)phenyl]acetic Acid Methyl ester	HCID 12971716	—

Reaction Steps

Following general procedure F and using 6-ethynyl-2,2,4,4-tetramethylchroman (synthesis described in U.S. Pat. Nos. 5,045,551 and 5,616,597 incorporated herein by reference) (0.060 g, 0.28 mmol), methyl-4-iodo phenyl acetate (Reagent B, 0.078 g, 0.28 mmol), triethyl amine (4 mL), tetrahydrofuran (4 mL), copper(I)iodide (0.030 g, 0.16 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.11 g, 0.16 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-10% ethyl acetate in hexane as the eluent the title compound was obtained (0.047 g, 46%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06531599B2
Source dataset	uspto-grants-2003_03
ORD ID	ord-87386b6e4ccb4d1ca42cb47ef42039b2
Source note	uspto-grants-2003_03