Reaction #321668

Reaction equation

benzylmagnesium chloride

5-chloroisatin

ammonium chloride

→

expected product

3-Benzyl-5-chloro-1,3-dihydro-3-hydroxyindol-2-one

Solvents

ether

THF

Conditions

Workup

1. 1
   Temperatureis cooled to +4° C.
2. 2
   Concentrationthe solvents are concentrated under vacuum
3. 3
   ExtractionThe aqueous phase is extracted with AcOEt
4. 4
   Washthe organic phase is washed with a saturated solution of NaCl and with water
5. 5
   Dryingdried over sodium sulfate
6. 6
   Otherthe solvent is evaporated off under vacuum

Procedure

A suspension of 10 g of 5-chloroisatin in 150 ml of THF is cooled to +4° C., 220 ml of a 1M solution of benzylmagnesium chloride in ether are added dropwise and the mixture is stirred for 3 hours at RT. 500 ml of a saturated solution of ammonium chloride are added and the solvents are concentrated under vacuum. The aqueous phase is extracted with AcOEt, the organic phase is washed with a saturated solution of NaCl and with water and dried over sodium sulfate and the solvent is evaporated off under vacuum to give 5.6 g of the expected product after crystallization from a THF/AcOEt mixture. M.p.=204°-205° C.

Source