反応 #1702083

反応方程式

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

収率 85.0%

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

収率 85.0%

溶媒

THF

DMF

反応条件

後処理

1. 1
   その他partitioned between water and ethyl acetate
2. 2
   抽出The aqueous phase was extracted with ethyl acetate
3. 3
   洗浄The combined organic layers were washed with 5% LiCl and brine
4. 4
   乾燥dried over magnesium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他The residue was purified by silica gel column chromatography

実験手順

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).

出典