反応 #172314

反応方程式

2-bromo-5-hydroxybenzaldehyde

(R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane

K2CO3

→

(S)-2-bromo-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzaldehyde

収率 56.0%

溶媒

DMF

water

反応条件

後処理

1. 1
   その他The resulting reaction mixture
2. 2
   温度cooled to room temperature
3. 3
   抽出extracted with EtOAc
4. 4
   乾燥The combined organic layers were dried (Na2SO4)
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他The resulting residue was purified by chromatography (petroleum ether/EtOAc=10:1

実験手順

To a solution of 2-bromo-5-hydroxybenzaldehyde (62; 5 g, 0.025 mol) in DMF (100 ml) was added (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (63; 4.87 g, 0.032 mol) and K2CO3 (7.0 g, 0.05 mol). The resulting reaction mixture was stirred at 150° C. for 10 h, cooled to room temperature, diluted with water, and then extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (petroleum ether/EtOAc=10:1 to afford the desired product, namely (S)-2-bromo-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzaldehyde 64 (4.1 g, 56%).

出典