反応 #2267136

反応方程式

Iodomethane

ethyl acetate

[(3R)-3-(5-chloro-2-cyanophenoxy)-3-(2-thiazolyl)propyl]-carbamic acid 1,1-dimethylethyl ester

sodium hydride

→

opaque oil

収率 98.0%

[(3R)-3-(5-Chloro-2-cyanophenoxy)-3-(2-thiazolyl)propyl]methylcarbamic acid 1,1-dimethylethyl ester

収率 98.0%

溶媒

isohexane

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction was stirred at room temperature for 18 h
2. 2
   その他quenched with saturated ammonium chloride solution
3. 3
   その他partitioned between ethyl acetate and water
4. 4
   洗浄The combined extracts were washed with water (3×25 ml) and saturated brine solution
5. 5
   乾燥dried (magnesium sulphate)
6. 6
   濃縮concentrated in vacuo
7. 7
   その他to leave a crude yellow gum

実験手順

To a solution of [(3R)-3-(5-chloro-2-cyanophenoxy)-3-(2-thiazolyl)propyl]-carbamic acid 1,1-dimethylethyl ester (200 mg, 0.51 mmol) in dry tetrahydrofuran (10 ml), was added sodium hydride (56 mg, 60% dispersion in oil, 1.41 mmol) and stirred at room temperature for 15 minutes. Iodomethane (1.325 g, 0.58 ml, 4.7 mmol) was added. The reaction was stirred at room temperature for 18 h, quenched with saturated ammonium chloride solution and partitioned between ethyl acetate and water. The combined extracts were washed with water (3×25 ml) and saturated brine solution, dried (magnesium sulphate) and concentrated in vacuo to leave a crude yellow gum. Flash chromatography (silica, 25% ethyl acetate in isohexane) afforded 175 mg of an opaque oil (98%).

出典