反应 #1702083

反应方程式

methyl 3-amino-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylate

1-Methoxy-1-oxo-1λ5 phosphinan-4-one

dibutyltin dichloride

phenylsilane

→

title compound

收率 85.0%

Methyl 5-(3,3-Dimethyl-but-1-ynyl)-3-(1-methoxy-1-oxo-1 λ5phosphinan-4-ylamino)-thiophene-2-carboxylate

收率 85.0%

溶剂

THF

DMF

反应条件

后处理

1. 1
   其他partitioned between water and ethyl acetate
2. 2
   萃取The aqueous phase was extracted with ethyl acetate
3. 3
   洗涤The combined organic layers were washed with 5% LiCl and brine
4. 4
   干燥dried over magnesium sulfate
5. 5
   过滤filtered
6. 6
   浓缩concentrated
7. 7
   其他The residue was purified by silica gel column chromatography

实验过程

A solution of methyl 3-amino-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylate (474 mg, 2 mmol) and 1-Methoxy-1-oxo-1λ5 phosphinan-4-one (390 mg, 2.4 mmol) in THF (1 mL) and DMF (1 mL) was treated with dibutyltin dichloride (60 mg, 0.2 mmol). After 5 min, phenylsilane (272 μL, 2.2 mmol) was added, and the mixture was stirred for one hour at room temperature and then partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with 5% LiCl and brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography using EtOAc:Hexanes as eluent to provide 650 mg (85%) of title compound: MS (m/z) 384.0 [M+H]+; HPLC retention time: 4.463 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

来源