Reaktion #1519097

Reaktionsgleichung

methanol

sodium hydride

Isatin

→

N-[4-(1,3-dioxolyl)phenyl]isatin

Lösungsmittel

chloroform

chloroform

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThis suspension was heated in an oil-bath at 135° C. under nitrogen for 16 hours
2. 2
   TemperaturIt was then cooled to room temperature
3. 3
   FiltrationThe resulting suspension was filtered
4. 4
   Einengenthe filtrate was concentrated under reduced pressure
5. 5
   Sonstigeevaporated to dryness
6. 6
   SonstigeA thick, viscous oil was recovered which
7. 7
   Sonstigesuch for the next reaction

Vorschrift

Isatin (1.88 g, 0.0128 moles) in anhydrous DMF (100 mL) was cooled in an ice bath under nitrogen and treated with sodium hydride (0.3 g, 1 equivalent). The reaction was warmed to room temperature and stirred for 1 hour. It was then treated with 2-(4-bromophenyl)-1,3-dioxalane (2.83 g, 0.0124 moles) followed by CuI (4.71 g, 2 equivalents). This suspension was heated in an oil-bath at 135° C. under nitrogen for 16 hours. It was then cooled to room temperature and diluted with an equal volume of chloroform. The resulting suspension was filtered and the filtrate was concentrated under reduced pressure. The residue was suspended in xylenes (100 mL) and evaporated to dryness. A thick, viscous oil was recovered which was used as such for the next reaction. TLC (5% methanol in chloroform) showed clean conversion, Rf (product)=0.91.

Quelle