Sodium hydride → HCID 58381705, compound

A solution of 3Z,6Z,9Z,12Z)-pentadeca-3,6,9,12-tetraene-1-thiol (9.80 g, 41.5 mmol) in dry dimethylformamide (DMF) (70 mL) at 0° C. under inert atmosphere was added NaH (60% in mineral oil, 1.82 g, 45.6 mmol) and stirred at this temperature for ten minutes. Ethyl bromobutyrate (6.39 mL, 43.5 mmol) was added and the mixture was stirred at ambient temperature for 30 minutes. The mixture was partitioned between saturated NH4Cl (150 mL) and heptane (150 mL). The aqueous layer was extracted twice with heptane (100 mL each) and the combined organic extract were washed with water (100 mL) and brine (100 mL). The organic layer was dried (Na2SO4), filtrated and concentrated. The residue was purification by flash chromatography on silica gel (heptane:EtOAc 99:1 then 95:5). Concentration of the appropriate fractions afforded 14.1 g (97% yield) of the title compound as oil.

1. stirringthe mixture was stirred at ambient temperature for 30 minutes
2. customThe mixture was partitioned between saturated NH4Cl (150 mL) and heptane (150 mL)
3. extractionThe aqueous layer was extracted twice with heptane (100 mL each)
4. extractionthe combined organic extract
5. washwere washed with water (100 mL) and brine (100 mL)
6. dry with materialThe organic layer was dried (Na2SO4)
7. filtrationfiltrated
8. concentrationconcentrated
9. custompurification by flash chromatography on silica gel (heptane:EtOAc 99:1

ORD record

ord-0ecb269a6cc24ad0bc87971905e8fff1

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759558B2