Reaction #6703

Reaction equation

methanol

sodium hydride

Isatin

→

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

Solvents

chloroform

chloroform

DMF

Conditions

Workup

1. 1
   TemperatureThis suspension was heated in an oil-bath at 135° C. under nitrogen for 16 hours
2. 2
   TemperatureIt was then cooled to room temperature
3. 3
   FiltrationThe resulting suspension was filtered
4. 4
   Concentrationthe filtrate was concentrated under reduced pressure
5. 5
   Otherevaporated to dryness
6. 6
   OtherA thick, viscous oil was recovered which
7. 7
   Othersuch for the next reaction

Procedure

Isatin (1.88 g, 0.0128 mol) 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 mol) 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.

Source