Reaktion #53266

Reaktionsgleichung

mesylate

Ethyl 6-methylsulfonyloxyhexanoate

Sodium hydride

alcohol

Hexaethylene glycol monobenzyl ether

NaH

→

product

Ausbeute 44.0%

6-{2-[2-(2-{2-[2-(2-Benzyloxyethoxy)ethoxy]ethoxy}-ethoxy)-ethoxy]-ethoxy}-hexanoic acid ethyl ester

Ausbeute 44.0%

Lösungsmittel

toluene

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled in an ice bath
2. 2
   Sonstigeto come to room temperature
3. 3
   workup.STIRRINGstirred for another five hours, during which time the mixture
4. 4
   workup.STIRRINGthe combined solutions were stirred at room temperature for three days
5. 5
   SonstigeThe reaction mixture was quenched with 50 ml methanol
6. 6
   Filtrationfiltered through basic alumina
7. 7
   EinengenThe filtrate was concentrated in vacuo
8. 8
   Sonstigepurified by flash chromatography (silica gel, gradient elution: 3/1 ethyl acetate/hexanes to ethyl acetate)

Vorschrift

Sodium hydride (3.225 g or a 60% oil dispersion, 80.6 mmol) was suspended in 80 ml of anhydrous toluene, placed under a nitrogen atmosphere and cooled in an ice bath. A solution of the non-polydispersed alcohol 16 (27.3 g, 73.3 mmol) in 80 ml dry toluene was added to the NaH suspension. The mixture was stirred at 0° C. for thirty minutes, allowed to come to room temperature and stirred for another five hours, during which time the mixture became a clear brown solution. The non-polydispersed mesylate 17 (19.21 g, 80.6 mmol) in 80 ml dry toluene was added to the NaH/alcohol mixture, and the combined solutions were stirred at room temperature for three days. The reaction mixture was quenched with 50 ml methanol and filtered through basic alumina. The filtrate was concentrated in vacuo and purified by flash chromatography (silica gel, gradient elution: 3/1 ethyl acetate/hexanes to ethyl acetate) to yield the non-polydispersed product as a pale yellow oil (16.52 g, 44%). FAB MS: m/e 515 (M+H).

Quelle