Reaction #806246

Reaction equation

ammonium chloride

ethyl tetrahydrofurancarboxylate

magnesium

1,4-dibromobutane

→

1-(2-tetrahydrofuranyl)cyclopentanol

Yield 89.9%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise at 50° C
2. 2
   workup.ADDITIONAfter the completion of dropwise addition
3. 3
   workup.STIRRINGThe solution was stirred at room temperature for one hour

Procedure

A flask was charged with 13.6 g of magnesium and 300 ml of tetrahydrofuran, to which 60.3 g of 1,4-dibromobutane was added dropwise at 50° C. After the completion of dropwise addition, the solution was stirred at 60° C. for one hour. To the solution below 40° C., 31.0 g of ethyl tetrahydrofurancarboxylate was added dropwise. The solution was stirred at room temperature for one hour, after which an aqueous solution of ammonium chloride was added for hydrolysis. Ordinary post-treatment yielded 30.2 g of 1-(2-tetrahydrofuranyl)cyclopentanol.

Source