Reaktion #1438215

Reaktionsgleichung

Water

product

1-Phenyl-2,5,8,11,14,17-hexaoxanonadecan-19-ol

potassium tert-butoxide

product

2-[2-(2-Methoxyethoxy)ethoxy]ethyl 4-methylbenzenesulfonate

→

title compound

Ausbeute 80.2%

1-Phenyl-2,5,8,11,14,17,20,23,26,29-decaoxatriacontane

Ausbeute 80.2%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturmaintaining the temperature at about −20° C
2. 2
   workup.STIRRINGAfter stirring at −20° C. for a further 3 hours
3. 3
   Temperaturto warm to 20° C.
4. 4
   workup.STIRRINGstirred for 16 hours
5. 5
   Einengenthe resultant mixture was concentrated in vacuo to 140 mL
6. 6
   workup.ADDITIONSodium chloride (12.5 g) was added to the stirred
7. 7
   Einengenconcentrate
8. 8
   Waschenwhich was then washed with diisopropyl ether (4×125 mL)
9. 9
   workup.ADDITIONThe aqueous phase was diluted with water (50 mL)
10. 10
    Extraktionextracted with dichloromethane (3×125 mL)
11. 11
    EinengenThe combined dichloromethane extracts were concentrated in vacuo

Vorschrift

To a stirred solution of the product of step (b) (25 g) in tetrahydrofuran (500 mL) at −20° C. was added a solution of potassium tert-butoxide in tetrahydrofuran (1.61M, 50 mL) over 1 hour, maintaining the temperature at about −20° C. The reaction mixture was stirred for a further 15 minutes then a solution of the product of step (a) (29.7 g) in tetrahydrofuran (100 mL) was added over 90 minutes, maintaining the temperature at about −20° C. After stirring at −20° C. for a further 3 hours, the mixture was allowed to warm to 20° C. and stirred for 16 hours. Water (125 mL) was then added and the resultant mixture was concentrated in vacuo to 140 mL. Sodium chloride (12.5 g) was added to the stirred concentrate, which was then washed with diisopropyl ether (4×125 mL). The aqueous phase was diluted with water (50 mL) and extracted with dichloromethane (3×125 mL). The combined dichloromethane extracts were concentrated in vacuo to give the title compound as an orange-brown oil (27.93 g). GC retention time 21.8 mins

Quelle