Pyridine → HCID 69305966, compound

Temperature

0 °C

Dry dichloromethane (5 mL), DMF (3.04 mL, 39.2 mmol) and a magnetic stir bar were placed into a 250 mL RBF, and the RBF was sealed with a rubber septum. N2 inlet and outlet needles were inserted into the septum. The flask was then cooled to 0° C. in an ice bath. Thionyl chloride (2.86 mL, 39.2 mmol) was added to the RBF via a syringe. The RBF was placed into an ice bath and cooled to 0° C. 3,5-diundecoxybenzyl alcohol (15.0 g, 35.7 mmol) was dissolved in a solution of dichloromethane (60 mL) and pyridine (2.88 mL, 35.7 mmol). This solution was added to the RBF via a syringe cautiously over 20 minutes. The reaction mixture gradually changed from a transparent yellow color to an opaque yellow color. The beaker used to dissolve the 3,5-diundecoxybenzyl alcohol was rinsed with dichloromethane and the rinses were added to the RBF. The RBF was removed from the ice bath and the reaction mixture was stirred overnight. The solution was then concentrated using rotary evaporation. A solution of 50/50 ether/hexanes (100 mL) was added to the RBF, changing the solution color from deep yellow to opaque white. The liquid was decanted leaving behind any solid. The RBF was rinsed in this manner 2 more times, saving the decanted liquid. The decanted liquid was run through a silica gel baseline filtration apparatus. The filtrate was then concentrated using rotary evaporation. The compound solidified after approximately 2 hours under high vacuum. This produced a 14.8 g yield or a 94.5% yield of the derivative. The NMR characterization data for the derivative is as follows. 1NMR (300 MHz, CDCl3): 0.88 (t, J=6.9, 6H, CH2CH3), 1.27-1.45 (m, 32H, CH2(CH2)8), 1.76 (p, J=6.6, 4H, OCH2CH2), 3.92 (t, J=6.6, 4H, OCH2), 4.50 (s, 2H, ArCH2Cl), 6.39 (t, J=2.2, 1H, ArH), 6.50 (d, J=2.2, 2H, ArH). 13C NMR (75 MHz, CDCl3): 14.23, 22.79, 26.13, 29.31, 29.45, 29.48, 29.68, 29.71, 32.01, 46.56, 68.19, 101.32, 106.97, 139.38, 160.53.

1. customthe RBF was sealed with a rubber septum
2. customN2 inlet and outlet needles were inserted into the septum
3. customThe RBF was placed into an ice bath
4. temperaturecooled to 0° C
5. additionThis solution was added to the RBF via a syringe cautiously over 20 minutes
6. washwas rinsed with dichloromethane
7. additionthe rinses were added to the RBF
8. customThe RBF was removed from the ice bath
9. concentrationThe solution was then concentrated
10. customevaporation
11. additionA solution of 50/50 ether/hexanes (100 mL) was added to the RBF
12. customThe liquid was decanted
13. customleaving behind any solid
14. washThe RBF was rinsed in this manner 2 more times
15. filtrationThe decanted liquid was run through a silica gel baseline filtration apparatus
16. concentrationThe filtrate was then concentrated
17. customevaporation
18. waitThe compound solidified after approximately 2 hours under high vacuum
19. customThis produced a 14.8 g
20. customyield

ORD record

ord-e551913a0b3f4c6da7f4ae35ed13956f

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07332529B2