Ethyl oxoacetate → HCID 89775040, compound

A 100 mL round bottom flask was charged with magnesium turnings (263 mg, 10.9 mmol) and a stirbar. The flask was dried with a heat gun for 5 minutes, cooled under nitrogen before THF (5 mL) and a small grain of iodine was added. A solution of (Z)-1-bromodec-4-ene 3 (2 g, 9.1 mmol) in THF (5 mL) was added slowly. The solution was stirred at room temperature for 2 hours then ethyl glyoxylate (0.375 mL, 1.82 mmol, 50% solution in toluene) was added. Upon completion, the solution was quenched with saturated ammonium chloride solution (5 mL) and stirred until the excess magnesium had dissolved. The solution was diluted with water and extracted with ethyl acetate (3×50 mL). The combined extracts were dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography (100% Hexanes to 20% EtOAc in hexanes) to afford (6Z,16Z)-11-((Z)-dec-4-enyl)docosa-6,16-diene-11,12-diol 29 as a colorless oil (700 mg, 48%).

1. customThe flask was dried with a heat gun for 5 minutes
2. temperaturecooled under nitrogen before THF (5 mL)
3. additiona small grain of iodine was added
4. customUpon completion, the solution was quenched with saturated ammonium chloride solution (5 mL)
5. stirringstirred until the excess magnesium
6. dissolutionhad dissolved
7. additionThe solution was diluted with water
8. extractionextracted with ethyl acetate (3×50 mL)
9. customThe combined extracts were dried on magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo to dryness
12. customThe residue was purified by column chromatography (100% Hexanes to 20% EtOAc in hexanes)

ORD record

ord-ffcc59b39346495c841fd579f3183f07

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09352042B2