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ChemicalBook CAS DataBase List 8-PENTADECANONE
818-23-5

8-PENTADECANONE synthesis

12synthesis methods
-

Yield:818-23-5 65%

Reaction Conditions:

in tetrahydrofuran at 0 - 20; for 4 h;Inert atmosphere;Solvent;

Steps:

5.2 ATX-81: Step 2
To a solution of 22 g heptyl magnesium bromide (1.5 eq.) in THF (100 ml), taken in a 1 liter, two neck round bottom flask, stirred at 0° C. under nitrogen atmosphere, was added N-methoxy-N-methyloctanamide (1 eq.) solution (dissolved in 200 ml THF) and the resulting reaction mixture was stirred at room temperature for 4 hours. Progress of the reaction was monitored by TLC (10% EtOAc in hexane; Rf: 0.7). Reaction mass was quenched with saturated NH4Cl solution (250 ml) and then EtOAc (350 ml) was added. The organic layer was separated and the aqueous layer was washed with EtOAc (2×100 ml). Combined organic layers were concentrated under reduced pressure. Crude compound was subjected to column chromatography using (60-120 mesh silica gel; 2% EtOAc/hexane). Quantity produced, 22 g; yield, 65%.

References:

Arcturus Therapeutics, Inc.;Payne, Joseph E.;Chivukula, Padmanabh;Karmali, Priya;Tanis, Steven P. US2018/169268, 2018, A1 Location in patent:Paragraph 0022; 0254-0256; 0418

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