Triphenylphosphine → HCID 58381698, compound

Temperature

0 °C

Triphenylphosphine (21.0 g, 80 mmol) was dissolved in dry THF (170 mL) at 0° C. under inert atmosphere and added DIAD (15.8 mL, 80 mmol) dropwise. After 40 minutes at 0° C. the white suspension was added dropwise to a solution of (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaen-1-ol (11.5 g, 40 mmol) and thioacetic acid (5.7 mL, 80 mmol) in dry THF (50 mL) during 15 minutes. The resulting turbid mixture was stirred at 0° C. for 30 minutes, followed by ambient temperature for 1.5 hour. Heptane was added (200 mL), the mixture was stirred for ten minutes and the precipitated white solid removed by filtration and rinsed with heptane (150 mL). The residue was concentrated to remove most of the THF and stirred at ambient for 18 hours. The mixture was filtered, concentrated and added heptane (200 mL). The resulting mixture was stirred for 2 hours, filtered and evaporated. The residue was purified by flash chromatography on silica gel, using EtOAc:Heptane (2:98), followed by EtOAc:Heptane (4:96) and finally EtOAc:Heptane (5:95). Concentration of the appropriate fractions provided 11.0 g (79% yield) of the title compound as oil.

1. waitfollowed by ambient temperature for 1.5 hour
2. stirringthe mixture was stirred for ten minutes
3. customthe precipitated white solid removed by filtration
4. washrinsed with heptane (150 mL)
5. concentrationThe residue was concentrated
6. customto remove most of the THF
7. stirringstirred at ambient for 18 hours
8. filtrationThe mixture was filtered
9. concentrationconcentrated
10. additionadded heptane (200 mL)
11. stirringThe resulting mixture was stirred for 2 hours
12. filtrationfiltered
13. customevaporated
14. customThe residue was purified by flash chromatography on silica gel

ORD record

ord-2c7c0fa7108f491db856cdf084b8b11f

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759558B2