تفاعل #816412

ord-45db47693dc64f1a8ba901b39e242d89

معادلة التفاعل

O=CNc1ccsc1I
product
O=CNc1ccsc1I
2-Iodo-3-formylaminothiophene
C#C[Si](C)(C)C
ethinyl trimethylsilane
C[Si](C)(C)C#Cc1sccc1NC=O
2-(trimethylsilylethinyl)-3-formamido-thiophene
المردود 95.3%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONwas added dropwise
  2. 2
    أخرىAfter 6 hours the solvents were removed under vacuum
  3. 3
    أخرىthe residue was chromatographed on silica gel (hexane:ethyl acetate 2:1)

الإجراء التجريبي

The product from step A (37.8 g) was dissolved in a mixture of DMF (500 ml) and triethylamine (50 ml). CuI (1.4 g) and bis(triphenylphosphino)palladiumdichloride (5.2 g) were added under nitrogen and after 15 minutes ethinyl trimethylsilane (22 g) was added dropwise. After 6 hours the solvents were removed under vacuum and the residue was chromatographed on silica gel (hexane:ethyl acetate 2:1) to yield 2-(trimethylsilylethinyl)-3-formamido-thiophene (31.78 g) (m.p. 87-93° C.).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07582589B2uspto-grants-2009_09