反応 #1514937

反応方程式

(E)-(2R,3R,4S,5S)-3,5-Dimethoxy-2,4-dimethyl-nona-6,8-dienal

2-methyl-2-butene

sodium chlorite

sodium dihydrogenphosphate

hydrochloric acid

→

product 3c

収率 79.4%

(E)-(2R,3R,4S,5S)-3,5-Dimethoxy-2,4-dimethyl-nona-6,8-dienoic acid

収率 79.4%

溶媒

brine

tert-butanol

water

反応条件

後処理

1. 1
   抽出The reaction was extracted with dichloromethane (3×)
2. 2
   その他the organics dried through a hydrophobic frit
3. 3
   濃縮concentrated in vacuo
4. 4
   workup.WAITThe oily residue was left on a vacuum pump overnight

実験手順

To (E)-(2R,3R,4S,5S)-3,5-Dimethoxy-2,4-dimethyl-nona-6,8-dienal (1.2 g, 5.3 mmol) in tert-butanol (24 ml) and 2-methyl-2-butene (5.6 ml, 53.1 mmol) at room temperature, was added a solution of sodium chlorite (2.4 g, 26.5 mmol) and sodium dihydrogenphosphate (1.5 g, 10.6 mmol) in water (5 ml). The reaction was stirred vigorously for 1.5 hours, after which brine (10 ml) was added and the reaction acidified to pH5 with 2M hydrochloric acid. The reaction was extracted with dichloromethane (3×), the organics dried through a hydrophobic frit and concentrated in vacuo. The oily residue was left on a vacuum pump overnight to afford the product 3c as an orange solid (1.02 g, 79%). 1H NMR (300 MHz, CDCl3) δ 6.39 (dt, J=16.7 Hz, 10.3 Hz, 10.0 Hz, 1H), 6.23 (dd, J=14.9 Hz, 10.5 Hz, 1H), 5.45 (dd, J=14.9 Hz, 8.7 Hz, 1H), 5.26 (d, J=16.3 Hz, 1H), 5.14 (d, J=10.3 Hz, 1H), 3.91 (dd, J=9.4 Hz, 1.8 Hz, 1H), 3.46 (s, 3H), 3.43 (m, 1H), 3.26 (s, 3H), 2.67 (m, 1H), 1.71 (m, 1H), 1.13 (d, J=7.1 Hz, 3H), 0.78 (d, J=7.1 Hz, 3H).

出典