反应 #56750

反应方程式

water

[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]-methanol

brosyl chloride

triethylamine

→

title compound

收率 76.9%

[(2R)-8-Methyl-2,3-Dihydro[1,4]Dioxino[2,3-f]Quinolin-2-yl]Methyl 4-Bromobenzenesulfonate

收率 76.9%

溶剂

isopropyl alcohol

toluene

toluene

反应条件

后处理

1. 1
   其他the two layers were separated
2. 2
   萃取The organic layer was extracted with 8% NaHCO3 (20 mL) and H2O (20 mL)
3. 3
   干燥dried over Na2SO4
4. 4
   过滤filtered
5. 5
   浓缩concentrated in vacuo
6. 6
   其他The solid obtained
7. 7
   过滤then filtered
8. 8
   洗涤washed with (5:1) IPA
9. 9
   干燥toluene (2×5 mL) and dried in a vacuum oven

实验过程

A solution of [(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]-methanol (4.0 g, 17.3 mmol), brosyl chloride (4.86 g, 19.0 mmol), dimethylamino pyridine (20 mg, 0.16 mmol) and triethylamine (3.62 mL, 25.8 mmol) in toluene (40 mL) was stirred at 60° C. for 6 h. The reaction mixture was cooled to room temperature then water (20 mL) was added. After 30 min, the two layers were separated. The organic layer was extracted with 8% NaHCO3 (20 mL) and H2O (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The solid obtained was dissolved in isopropyl alcohol (50 mL) and toluene (10 mL) at 80° C., cooled to room temperature over 1 h then filtered, washed with (5:1) IPA: toluene (2×5 mL) and dried in a vacuum oven to give 5.99 g (76.9%) of the title compound as an off-white solid. 13C NMR (CDCl3) δ 157.9, 144.3, 138.1, 134.7, 132.9, 129.7, 129.6, 129.0, 122.4, 121.7, 121.3, 118.8, 70.7, 67.6, 64.5, 25.4

来源