반응 #1702083

반응 방정식

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

수율 85.0%

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

수율 85.0%

용매

THF

DMF

반응 조건

후처리

1. 1
   기타partitioned between water and ethyl acetate
2. 2
   추출The aqueous phase was extracted with ethyl acetate
3. 3
   세척The combined organic layers were washed with 5% LiCl and brine
4. 4
   건조dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The residue was purified by silica gel column chromatography

실험 절차

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).

출처