Réaction #5635

Équation de réaction

Compound 15

6-dodecyl-6-(2-hydroxybenzyl)-13,13-dimethyl-1,4,8,11-tetraoxacyclotetradecane

2-methylsulfonyl-4-nitrophenyldiazonium hexafluorophosphate

→

Compound 16

Rendement 4.9%

6-Dodecyl-6-[2-hydroxy-5-(2-methylsulfonyl-4-nitrophenylazo)benzyl]-13,13-dimethyl-1,4,8,11-tetraoxacyclotetradecane

Rendement 4.9%

Solvants

acetic acid

water

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   ExtractionThe product was extracted into ethyl acetate
2. 2
   Autreisolated by silica gel chromatography

Mode opératoire

To a solution of 3.1 g (6.1 mmol) of Compound 15 in 50 cc acetic acid at 5° C. was added a solution of 3.0 g (8.0 mmol) of 2-methylsulfonyl-4-nitrophenyldiazonium hexafluorophosphate in 25 cc water and 75 cc tetrahydrofuran. The suspension was stirred at room temperature for 16 hours. The product was extracted into ethyl acetate and isolated by silica gel chromatography yielding 0.22 g (4.7%) of Compound 16. The 1H NMR spectrum is consistent with the assigned structure.

Source