反応 #1438215

反応方程式

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

収率 80.2%

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

収率 80.2%

溶媒

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

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

実験手順

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

出典