Reaction #443411

Reaction equation

4-bromobutanol

3,4-dihydro-2H-pyran

sodium hydrogencarbonate

→

4-(tetrahydropyran-2-yl)oxybutyl bromide

Yield 96.0%

Solvents

chloroform

chloroform

Conditions

Workup

1. 1
   Othera solution prepared
2. 2
   workup.ADDITIONwas dropwise added
3. 3
   Otherat 0° C.
4. 4
   OtherThe solution obtained
5. 5
   Otherat 0° C.
6. 6
   Extractionthe resulting solution was extracted with chloroform (100 ml×2)
7. 7
   OtherThe organic layer obtained
8. 8
   Dryingwas dried with anhydrous sodium sulfate
9. 9
   Concentrationconcentrated under reduced pressure

Procedure

16.0 g (105.0 mmols) of 4-bromobutanol was dissolved in 140 ml of chloroform, and a solution prepared by dissolving 13.9 ml (1.5-fold equivalent weight) of 3,4-dihydro-2H-pyran in 40 ml of chloroform was dropwise added thereto at 0° C. in an atmosphere of argon. The solution obtained was stirred for 4 hours while keeping it at 0° C., followed by addition of an aqueous sodium hydrogencarbonate, and the resulting solution was extracted with chloroform (100 ml×2). The organic layer obtained was dried with anhydrous sodium sulfate, and thereafter concentrated under reduced pressure to obtain 24.0 g of 4-(tetrahydropyran-2-yl)oxybutyl bromide (yield: 96%).

Source