Reaction #2006444

Reaction equation

THF

[2-(2-Hydroxyethoxy)-ethyl]-carbamic acid anthracen-9-ylmethyl ester

sodium hydride

1-chloro-4-Iodobutane

→

product

Yield 32.0%

{2-[2-(4-Chlorobutoxy)-ethoxy]ethyl}-carbamic acid anthracen-9-ylmethyl ester

Yield 32.0%

Solvents

heptane

ethyl acetate

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction is stirred at room temperature for 24 hours

Procedure

A 50 ml round bottom flask was charged with [2-(2-Hydroxyethoxy)-ethyl]-carbamic acid anthracen-9-ylmethyl ester (0.25 g, 0.74 mmol) and fresh sodium hydride, 60% dispersion in mineral oil (150 mg, 3.75 mmol) under inert atmosphere. 10 ml anhydrous THF was added and the reaction allowed to stir for 5 minutes. After this point, 1-chloro-4-Iodobutane (180 μl, 1.5 mmol) is added via syringe. The reaction is stirred at room temperature for 24 hours. Silica gel 60 is co-absorbed onto the reaction mixture with loss of solvent under reduced pressure. Silica gel column chromatography takes place initially with heptane as eluent, followed by 10%, 20%, and 30% ethyl acetate. A total of 0.1 g (32% yield) of product is isolated from appropriate fractions:

Source