Triethoxysilane → 4-[2-(Thiophen-2-yl)ethenyl]morpholine

Temperature

60 °C

4-(2-[2-thienyl]acetyl) morpholine (0.42 g, 2.0 mmol) was dissolved in C6H6 (4 mL) and then triethoxysilane (0.92 mL, 5.0 mmol) and titanium (IV) isopropoxide (0.03 mL, 0.1 mmol) were added. The reaction mixture was heated to 60 ° C. for 15 hours. The C6H6 was removed in vacuo and the resulting yellow solid was dissolved in warm (60° C.) hexane (4 mL). The hexane solution was cooled to room temperature, and yellow crystals appeared in the flask. The recrystallization flask was put in an acetone-filled dewar, which was cooled to -78° C. overnight. The hexane solution was decanted from the yellow crystals. The crystals were washed with cold hexane (3 mL) and recrystallized from hot (60° C.) hexane. The flask containing the crystals was put in an acetone-filled dewar, which was cooled to -78° C. The hexane was decanted and the crystals were washed with 2 portions of cold hexane (1 mL). The crystals were dried in vacuo and 0.28 g (74% yield) of 4-(2-[2-thienyl]ethenyl) morpholine, as yellow crystals, was collected.

1. customThe C6H6 was removed in vacuo
2. dissolutionthe resulting yellow solid was dissolved
3. temperaturein warm (60° C.) hexane (4 mL)
4. temperatureThe hexane solution was cooled to room temperature
5. additionfilled dewar, which
6. temperaturewas cooled to -78° C. overnight
7. customThe hexane solution was decanted from the yellow crystals
8. washThe crystals were washed with cold hexane (3 mL)
9. customrecrystallized from hot (60° C.) hexane
10. additionThe flask containing the crystals
11. additionfilled dewar, which
12. temperaturewas cooled to -78° C
13. customThe hexane was decanted
14. washthe crystals were washed with 2 portions of cold hexane (1 mL)

ORD record

ord-39a7a0e432f54923bee0858990e2a4bd

Source dataset

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05220020