Réaction #2467950

Équation de réaction

THF

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

sodium hydride

1-chloro-4-Iodobutane

→

product

Rendement 32.0%

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

Rendement 32.0%

Solvants

heptane

ethyl acetate

Conditions de réaction

Traitement

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

Mode opératoire

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: 1H NMR (CDCl3) δ 8.50 (s, H-10), 8.40 (d, H-1, 8), 8.03 (d, H-4, 5), 7.53 (dt, H-2,3,6,7), 6.15 (s, CH2-anth), 5.19 (m, exchangeable, NH), 3.93-3.32 (m, 12H) 1.69-1.25 (m, 4H). Mass spectrum, m/e Calcd for C24H28ClNO4.H2O: 447.18 (100.0%); 448.18 (27.1%). Found: 447.17; 448.41.

Source