Cesium carbonate → 6-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

関与物質

役割	名称	HCID	仕込み量
反応物	Cesium carbonate	HCID 10796	—
反応物	Cesium iodide	HCID 24601	—
反応物	2-Bromo-1,1-dimethoxyethane	HCID 81672	—
反応物	6-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one	HCID 15908314	—
溶媒	Dimethylformamide	HCID 6228	—
溶媒	Sodium chloride; water	HCID 57417360	—
生成物	6-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline	HCID 18963883	—

反応手順

To a solution of 6-hydroxy-1-oxo-1,2,3,4-tetrahydroisoquinoline (25 g, 15.3 mmol), CsI (4 g, 15.3 mmol) and bromoacetaldehyde dimethyl acetal (40 ml, 338 mmol) in DMF (600 ml) is added Cs2CO3 (137.5 g, 460 mmol). The reaction mixture is heated at 60° overnight. After this time, the reaction is poured into 1 liter brine and the resulting suspension is extracted with EtOAc (4×400 ml). The combined EtOAc extracts are dried over MgSO4 and concentrated in vacuo. The residue is washed with Et2O to yield 6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline as a crystalline solid.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US05260316
出典データセット	uspto-grants-1993_11
ORD ID	ord-1742ff794edb415bb609e30f4ecef1d1
出典メモ	uspto-grants-1993_11