Diglyme → (1S,2R,4aS,8aS)-1-(2,4-dimethoxyphenoxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

関与物質

反応条件

反応手順

In a sealed tube purged with nitrogen, 1-iodo-2,4-dimethoxybenzene (40) (3.02 g, 11.4 mmol), (1S,2R,4aS,8aS)-1-(hydroxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (3) (2.50 g, 10.4 mmol), Cs2CO3 (5.10 g, 15.6 mmol), 3,4,7,8-tetramethyl-[1,10]-phenylthroline (0.50 g, 2.1 mmol), CuI (0.16 g, 1.0 mmol), diglyme (10 mL) and toluene (30 mL) were placed. The reaction mixture was stirred at 130° C. for 18 h. The reaction was cooled to room temperature, diluted with EtOAc (600 mL) and washed with water (200 mL). The solid material was removed by filtration. The organic layer was separated, dried (Na2SO4) and concentrated. Purification by column chromatography on silica gel (Hexanes/EtOAc, 4:1) gave (1S,2R,4aS,8aS)-1-(2,4-dimethoxyphenoxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (41) (2.50 g, 64%) as an off white solid.

情報源と証拠