反応 #42566

反応方程式

methyl 3-[(dipropylamino)carbonyl]-5-iodobenzoate

thiazole

n-butyl lithium

→

methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate

収率 99.1%

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度The mixture was then heated at 80° C. for 2 h, at which time it
3. 3
   温度to cool
4. 4
   その他partitioned between ethyl acetate and water
5. 5
   洗浄The organic layers were washed with brine
6. 6
   乾燥dried (magnesium sulfate)
7. 7
   濃縮concentrated
8. 8
   その他The residue was chromatographed on silica gel

実験手順

To a −78° C. solution of thiazole (1.2 g) in THF (25 mL) was added n-butyl lithium (1.6 M in hexanes, 10 mL). The mixture was stirred for 30 min and then allowed to warm to 0° C. in an ice/water bath. Zinc chloride (1M in ethyl ether, 40 mL) was added and the mixture was stirred for 1 h, at which time methyl 3-[(dipropylamino)carbonyl]-5-iodobenzoate (5.1 g) in THF (20 mL) was added, followed by Pd(PPh3)4 (palladium tetrakis triphenylphosphine) (0.68 g). The mixture was then heated at 80° C. for 2 h, at which time it was allowed to cool and partitioned between ethyl acetate and water. The organic layers were washed with brine, dried (magnesium sulfate), and concentrated. The residue was chromatographed on silica gel using ethyl acetate/heptane (50/50) to give 4.5 g of methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate.

出典