Diisopropylamine → 6-[2-cyclopentyl-4-(3-fluoro-4-isopropylphenyl)-2-hydroxybut-3-ynyl]-2,2-dimethyl-4H-1,3-dioxin-4-one

関与物質

役割	名称	HCID	仕込み量
反応物	Diisopropylamine	HCID 7912	—
反応物	4-Bromo-2-fluoro-1-(1-methylethyl)benzene	HCID 21051092	—
反応物	6-(2-Cyclopentyl-2-hydroxy-but-3-ynyl)-2,2-dimethyl-[1,3]dioxin-4-one	HCID 22499802	—
触媒	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
触媒	HCID 178418476	HCID 178418476	—
溶媒	Dimethylformamide	HCID 6228	—
溶媒	Ethyl Acetate	HCID 8857	—
生成物	6-[2-cyclopentyl-4-(3-fluoro-4-isopropylphenyl)-2-hydroxybut-3-ynyl]-2,2-dimethyl-4H-1,3-dioxin-4-one	HCID 58762587	89.2%

反応条件

温度	90 °C

反応手順

4-Bromo-2-fluoro-1-isopropylbenzene (5.0 g, 23.2 mmol), 6-(2-cyclopentyl-2-hydroxybut-3-ynyl)-2,2-dimethyl-4H-1,3-dioxin-4-one (5.56 g, 21.0 mmol) were dissolved in anhydrous DMF (30 mL). To this solution, CuI (120 mg, 0.63 mmol), Pd(PPh3)2Cl2 (0.59 g, 0.84 mmol), and diisopropylamine (60 mL), were added sequentially. The mixture was then heated at 90° C. for 20 min before it was cooled down to 25° C. The reaction was diluted with EtOAc (150 mL) and washed with aqueous NH4Cl, brine, and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash column chromatography (040% EtOAc in hexanes) to give the desired product (7.5 g, 81% yield).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07148226B2
出典データセット	uspto-grants-2006_12
ORD ID	ord-2caacc4625404161ba0665d00f684cee
出典メモ	uspto-grants-2006_12