反応 #63006

反応方程式

K2CO3

3-[1-(Ethoxy)ethoxy]-1-propene

O3

dimethyl sulfide

→

title product

2-[1-(Ethoxy)ethoxy)acetaldehyde

溶媒

ether

methanol

water

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他The aqueous layer was separated
3. 3
   workup.ADDITIONdiluted with brine
4. 4
   抽出extracted with fresh ether
5. 5
   その他dried

実験手順

3-[1-(Ethoxy)ethoxy]-1-propene (40 g., 0.0307 mol) was stirred in 100 ml. methanol at -78° for 5.5 hours as O3 was through the solution. The resulting pale blue solution was purged with H2, dimethyl sulfide (34 ml., 43.4 g., 0.68 mol) was added, and the mixture warmed to room temperature over 45 minutes. K2CO3 (0.2 g.) was added, the reaction mixture stripped of solvent, and the residue diluted with 1:1 water:ether. The aqueous layer was separated, diluted with brine and extracted with fresh ether. The organic layers were combined, dried and stripped to yield the title product as an oil, 15.25 g., 1H-nmr: 1.24 (t, 3H), 1.37 (d, 3H), 3.50 (s, 2H), 3.61 (m, 2H), 4.81 (m, 1H), 9.87 (s, 1H).

出典