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

Temperature

-20 °C

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

1. temperaturemaintaining the temperature at about −20° C
2. stirringAfter stirring at −20° C. for a further 3 hours
3. temperatureto warm to 20° C.
4. stirringstirred for 16 hours
5. concentrationthe resultant mixture was concentrated in vacuo to 140 mL
6. additionSodium chloride (12.5 g) was added to the stirred
7. concentrationconcentrate
8. washwhich was then washed with diisopropyl ether (4×125 mL)
9. additionThe aqueous phase was diluted with water (50 mL)
10. extractionextracted with dichloromethane (3×125 mL)
11. concentrationThe combined dichloromethane extracts were concentrated in vacuo

ORD record

ord-ac4e26b4f07147748b5b7bd372e5b42c

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07217409B2