反応 #1880955

反応方程式

water

(2E,7Z)-1,1-dimethoxy-2,4,7-decatriene

→

(2E,7Z)-2,4,7-decatrienal

収率 96.0%

溶媒

acetone

Et2O

反応条件

後処理

1. 1
   workup.ADDITIONwere added 0.2 g of AMBERLITE®
2. 2
   その他the reaction mixture so obtained
3. 3
   ろ過Afterwards, the reaction mixture was filtered
4. 4
   濃縮concentrated
5. 5
   その他The crude product thus obtained
6. 6
   洗浄the organic phase has been washed twice with brine
7. 7
   乾燥dried over Na2SO4
8. 8
   濃縮concentrated
9. 9
   その他to yield 8.8 g of an extract
10. 10
    workup.DISTILLATIONThe extract has been further purified by distillation over a Vigreux column (52–54° C./0.1 mbar)

実験手順

To a solution of 9.8 g of a mixture of (2E,7Z)-1,1-dimethoxy-2,4,7-decatriene as obtained in example 1 (50 mmoles) and 2.7 ml of water (150 mmoles) in 150 ml of acetone were added 0.2 g of AMBERLITE®, and the reaction mixture so obtained was stirred for 1 hour at room temperature. Afterwards, the reaction mixture was filtered and neutralized with 1 ml of a saturated aqueous solution of NaHCO3, and then concentrated. The crude product thus obtained was dissolved in Et2O and the organic phase has been washed twice with brine, dried over Na2SO4 and concentrated to yield 8.8 g of an extract. The extract has been further purified by distillation over a Vigreux column (52–54° C./0.1 mbar) to yield 7.2 g of a mixture of (2E,7Z)-2,4,7-decatrienal (4Z:4E=88:8)(purity=96%, yield=96%). The product thus obtained had the same spectroscopic data as described in WO 01/58282.

出典