反応 #76332

反応方程式

dioxane

aldehyde

3-bromo-4-(4-morpholinyl)benzaldehyde

2-(tributylstannyl)furan

KF

→

3-(2-furanyl)4-(4-morpholinyl)benzaldehyde

収率 84.0%

溶媒

ethyl acetate

反応条件

後処理

1. 1
   温度The mixture was heated
2. 2
   温度to reflux under argon for 18 h
3. 3
   ろ過The slurry was filtered through celite
4. 4
   その他The organic layer was separated
5. 5
   洗浄washed with brine
6. 6
   乾燥dried (MgSO4)
7. 7
   その他evaporated to a yellow oil
8. 8
   その他Purification by silica gel flash chromatography
9. 9
   洗浄eluting with 20% ethyl acetate in hexane

実験手順

Ex-604B) To a dioxane (8 mL) solution of the aldehyde from EX-604A (0.77 g, 2.8 mmol) was added 2-(tributylstannyl)furan (1.07 mL, 3.42 mmol) and Pd(PPh3)2Cl2 (0.12 g, 0.17 mmol). The mixture was heated to reflux under argon for 18 h. The cooled mixture was poured into a mixture of saturated aq. KF and ethyl acetate and stirred 3 h. The slurry was filtered through celite. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated to a yellow oil. Purification by silica gel flash chromatography eluting with 20% ethyl acetate in hexane gave 0.61 g (84%) of the desired 3-(2-furanyl)4-(4-morpholinyl)benzaldehyde product as a yellow oil. MS: m/z=258.1 [M+H]+.

出典