Triethylamine → HCID 58381726, compound

Temperature

0 °C

Et3N (1.50 mL, 10.8 mmol) and methanesulfonyl chloride (402 μL, 5.20 mmol) was added to a solution of (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaen-1-ol (1.15 g, 4.0 mmol) in CH2Cl2 (40 mL) held at 0° C. under nitrogen. The mixture was stirred at 0° C. for one hour, and poured into ice-water (100 g) and the water phase extracted with Et2O (50 mL). The combined organic extracts were added 0.5 M H2SO4 (35 mL), the organic phase washed with NaHCO3 (sat. aq.) (25 mL), before dried (Mg2SO4, gram). Filtration and concentration in vacuo afforded 1.24 gram of crude oil. Purification on Armen, SVP D26 column packed with 30 gram of 15-40 μm Merck silica, flow 20 mL/min, UV 210 nm and collecting 15 mL fraction, was performed using gradient elution: (starting heptane:EtOAc (100:0) and increasing during 10 min. to 10% EtOAc, then increasing 5 min. to 20% EtOAc (hold 10 min.), then increasing in 5 min. to 40% EtOAc (hold 0 min.). Fractions 6-14 afforded 1.16 g (79% yield) of the title compound as oil.

1. customheld at 0° C. under nitrogen
2. extractionthe water phase extracted with Et2O (50 mL)
3. additionThe combined organic extracts were added 0.5 M H2SO4 (35 mL)
4. washthe organic phase washed with NaHCO3 (sat. aq.) (25 mL)
5. dry with materialbefore dried (Mg2SO4, gram)
6. filtrationFiltration and concentration in vacuo
7. customafforded 1.24 gram of crude oil
8. customPurification on Armen, SVP D26 column
9. customcollecting 15 mL fraction
10. washelution
11. temperatureincreasing during 10 min. to 10% EtOAc
12. temperatureincreasing 5 min. to 20% EtOAc (hold 10 min.)
13. temperatureincreasing in 5 min. to 40% EtOAc (hold 0 min.)

ORD record

ord-0a01a45a69554812819ed7a40d1691aa

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759558B2