Reaction #1208

Reaction equation

15-(2-tetrahydropyranyloxy)pentadecanal

dimethyl sulfoxide

N2

sodium hydride

dimethyl sulfoxide

water

→

1-(2-tetrahydropyranyloxy)-15-hexadecene

Yield 46.0%

Solvents

THF

Conditions

Workup

1. 1
   OtherA 300-ml three-necked flask equipped with a stirrer
2. 2
   OtherAfter completion of the reaction
3. 3
   Extractionsubjected to extraction with hexane
4. 4
   Concentrationfollowed by concentration under reduced pressure
5. 5
   OtherThereafter, the resultant residue was purified by flash column chromatography on silica gel

Procedure

A 300-ml three-necked flask equipped with a stirrer, dropping funnel and N2 inlet tube was charged with 40 ml of dimethyl sulfoxide and 1.2 g (30 mmol) of 60% sodium hydride. The contents were stirred at 75° C. for 1.5 hours in an N2 atmosphere and then cooled to room temperature. To this mixture, a solution of 8.93 g (25 mmol) of methyltriphenylphosphonium bromide in 40 ml of dimethyl sulfoxide was added dropwise over 10 minutes. The resultant mixture was stirred further for 20 minutes at room temperature. To this mixture, a solution of 3.27 g (10 mmol) of 15-(2-tetrahydropyranyloxy)pentadecanal in 15 ml of THF was added dropwise over 5 minutes, followed by stirring further for 30 minutes. After completion of the reaction, the reaction mixture was added with water and subjected to extraction with hexane, followed by concentration under reduced pressure. Thereafter, the resultant residue was purified by flash column chromatography on silica gel, thereby obtaining 1.49 g (yield: 46%) of 1-(2-tetrahydropyranyloxy)-15-hexadecene.

Source