Reaction #1880

Reaction equation

trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-methanol

Jones reagent

→

trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-carboxylic acid

Solvents

acetone

Conditions

Workup

1. 1
   workup.ADDITIONTo the solution was added dropwise
2. 2
   workup.STIRRINGThe reaction mixture was stirred for one hour at room temperature
3. 3
   Concentrationwhich was then concentrated under reduced pressure The concentrate
4. 4
   Extractionwas subjected to extraction with ethyl acetate
5. 5
   WashThe organic layer was washed with water
6. 6
   Otherdried
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Procedure

In 20 ml of acetone was dissolved 0.5 g of trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-methanol obtained in Example 46. To the solution was added dropwise, while stirring at room temperature, 0.5 ml of a Jones reagent. The reaction mixture was stirred for one hour at room temperature, which was then concentrated under reduced pressure The concentrate was subjected to extraction with ethyl acetate. The organic layer was washed with water and dried, then the solvent was distilled off under reduced pressure. From the residue was obtained 0.23 g of trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-carboxylic acid as white crystals, m.p.177°-178 C.

Source