反応 #2146726

反応方程式

9

Dimethyl 5-(2,5-dimethyl-1H-pyrrol-1-yl)isophthalate

Dibal-H

→

10

収率 97.0%

(5-(2,5-Dimethyl-1H-pyrrol-1-yl)-1,3-phenylene)dimethanol

収率 97.0%

溶媒

THF

反応条件

後処理

1. 1
   その他quenched by sodium potassium tartrate (1 M, 40 mL) The THF
2. 2
   その他was removed by rotary evaporation
3. 3
   抽出the resulting aqueous solution was extracted by ether (3×100 mL) The combined organic layers
4. 4
   乾燥were dried over Na2SO4
5. 5
   濃縮concentrated
6. 6
   その他The crude product was purified by flash column chromatography (EtOAc/hexanes, 2:1-4:1)

実験手順

To a solution of 9 (2.87 g, 10 mmol) in THF (60 mL) at −78° C. was added Dibal-H (1 M solution in toluene, 60 mL, 60 mmol) drop wise. The reaction mixture was slowly warmed to room temperature over a period of 6 h, and then quenched by sodium potassium tartrate (1 M, 40 mL) The THF was removed by rotary evaporation, and the resulting aqueous solution was extracted by ether (3×100 mL) The combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography (EtOAc/hexanes, 2:1-4:1) to yield 10 (2.24 g, 97%) as a white solid (Caution: the product is not stable as solution forms, while stable in solid form for weeks at room temperature): 1H NMR (500 MHz, CDCl3) δ 2.01 (s, 6H), 2.45 (s, 2H), 4.69-4.70 (d, J=5.5 Hz, 4H), 5.89 (s, 2H), 7.10 (s, 2H), 7.39 (s, 1H); 13C NMR (125 MHz, CDCl3) δ 13.1, 64.5, 105.8, 124.3, 125.6, 128.7, 139.3, 142.4; LC-MS (M+H+) calcd for C14H18NO2 232, found 232.

出典