Lauric Acid → Methyl 3-oxotetradecanoate

To a suspension of magnesium ethoxide (10.82 g, 94.61 mmol) in 1,4-dioxane (100 mL) was added methyl hydrogen malonate (25.0 g, 189 mmol) in 1,4-dioxane (100 mL). The resulting slurry was stirred overnight. The mixture was concentrated in vacuo. In a separate flask, lauric acid (28, 20.85 g, 104.1 mmol) was dissolved in 1,4-dioxane (50 mL) and a solution of CU (16.88 g, 104.1 mmol) in 1,4-dioxane (150 mL) was added at room temperature. The resulting solution was stirred overnight. The mixture was then transferred to the methyl magnesium malonate flask. The resulting suspension was refluxed overnight. The mixture was concentrated in vacuo. The residue was redissolved in DCM (300 mL) and filtered through a silica plug (10 g). The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (360 g RediSep column, eluting with a gradient of 0% through 30% ethyl acetate/hexanes over 80 min, 100 mL/min) to afford product 29 (17 g, 61%) as a pale yellow syrup.

1. concentrationThe mixture was concentrated in vacuo
2. stirringThe resulting solution was stirred overnight
3. temperatureThe resulting suspension was refluxed overnight
4. concentrationThe mixture was concentrated in vacuo
5. dissolutionThe residue was redissolved in DCM (300 mL)
6. filtrationfiltered through a silica plug (10 g)
7. customThe solvent was evaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (360 g RediSep column
9. washeluting with a gradient of 0% through 30% ethyl acetate/hexanes over 80 min

ORD record

ord-1964871a6f504eeda175f07589fd8e28

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722064B2