反応 #40882

反応方程式

Ammonium chloride

methanol

ethyl (2E)-3-(2,4-dichlorophenyl)acrylate

diisobutylaluminium hydride

→

title compound

収率 83.5%

(2E)-3-(2,4-dichlorophenyl)prop-2-en-1-ol

収率 83.5%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONAfter addition
2. 2
   温度to warm to 0° C
3. 3
   温度to warm to room temperature
4. 4
   ろ過The mixture was then filtered through a pad of hyflo supercel (
5. 5
   洗浄washing well with ethyl acetate) and the
6. 6
   濃縮concentrated

実験手順

To a stirred solution of ethyl (2E)-3-(2,4-dichlorophenyl)acrylate (11.3 g, 46 mmol) in tetrahydrofuran at −10° C. was added diisobutylaluminium hydride (1.0 M in toluene, 100 ml, 0.11 mol) dropwise. After addition was complete, the reaction was cooled to −78° C. and methanol (40 ml) added dropwise. Ammonium chloride (sat. aq., 70 ml) was then added and the reaction allowed to warm to 0° C. After 15 min at 0° C. the reaction was allowed to warm to room temperature and stirred for 1 h. The mixture was then filtered through a pad of hyflo supercel (washing well with ethyl acetate) and the concentrated to give the title compound (7.8 g) as pale yellow crystals. 1H NMR δ (ppm)(CDCl3): 7.44 (1 H, d, J=8.4 Hz), 7.36 (1 H, d, J=2.0 Hz), 7.19 (1 H, dd, J=2.0, 8.5 Hz), 6.93 (1 H, d, J=15.8 Hz), 6.36-6.28 (1 H, m), 4.35 (2 H, d, J=5.4 Hz), 1.84 (1 H, s).

出典