Sodium Azide → HCID 57459968, Verbindung

A mixture of 12-bromo-1-dodecanol (246 mg, 0.927 mmol) in t-butanol (1.8 mL, 0.5 M) was treated with sodium azide (121 mg, 1.855 mmol, 2 eq), tetrabutylammonium iodide (17 mg, 0.0464 mmol, 0.05 eq) and sat. aq. sodium bicarbonate solution (0.9 mL) in that order. The mixture was stirred at room temperature for 4 days. The mixture was filtered through a plug of celite and the cake rinsed with ethyl acetate (20 mL). The combined filtrate and washings were evaporated onto silica gel and purified by flash column (2.5×18 cm, gradient elution with hexane-ethyl acetate 6:1, 4:1 to 2:1) to give 12-Azido-1-dodecanol as a colourless oil (193 mg, 92%). 1H NMR (CDCl3, 400 MHz): 3.62 (t, 2H, J=7.0, OCH2), 3.24 (t, 2H, J=7.0, NCH2), 1.61-1.51 (m, 4H), 1.35-1.25 (m, 16H).

1. filtrationThe mixture was filtered through a plug of celite
2. washthe cake rinsed with ethyl acetate (20 mL)
3. customThe combined filtrate and washings were evaporated onto silica gel
4. custompurified by flash column (2.5×18 cm, gradient elution with hexane-ethyl acetate 6:1, 4:1 to 2:1)

ORD-Eintrag

ord-e37202d94ea64e499d0f22ef85793fe5

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08828952B2