反応 #1265388

反応方程式

1-Thiazol-2-yl-ethanone

trimethyl orthoformate

p-toluenesulfonic acid

→

sub-title compound

2-(1,1-Dimethoxy-ethyl)-thiazole

溶媒

methanol

反応条件

後処理

1. 1
   温度The mixture was cooled to ambient and
2. 2
   濃縮concentrated
3. 3
   その他partitioned between saturated sodium bicarbonate and diethyl ether (100 ml)
4. 4
   その他The organic phase was removed
5. 5
   洗浄washed with saturated sodium bicarbonate and brine
6. 6
   乾燥dried (magnesium sulfate)
7. 7
   ろ過filtered
8. 8
   濃縮concentrated

実験手順

To a solution of 1-Thiazol-2-yl-ethanone (7 g) in dry methanol (100 ml) was added trimethyl orthoformate (35 ml) and p-toluenesulfonic acid (10 g) and the resulting mixture was heated at 50° C. for 12 hours. The mixture was cooled to ambient and concentrated, partitioned between saturated sodium bicarbonate and diethyl ether (100 ml). The organic phase was removed and washed with saturated sodium bicarbonate and brine, dried (magnesium sulfate), filtered and concentrated to afford the sub-title compound as crude product. The product could be further purified if necessary by flash chromatography (20% ethyl acetate/petroleum ether) to afford the sub-title compound in quantitative yield as yellow oil (9.5 g); 1H NMR (400 Mhz, CDCl3) δ 1.75 (3H, s), 3.25 (6H, s), 7.3 (1H, s), 7.85 (1H, s); MS (ES+) 174.1 (M+1).

出典