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ChemicalBook CAS DataBase List 7-TRIDECANONE

7-TRIDECANONE synthesis

5synthesis methods
From Hexyl magnesium chloride and Heptyl nitrile (Hexyl cyanide).
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Yield:462-18-0 65%

Reaction Conditions:

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

Steps:

7.2 ATX-86: Step 2
To a solution of hexyl 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 38 g 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, 44 g; yield, 65%; confirmed by Mass.

References:

Arcturus Therapeutics, Inc.;Payne, Joseph E.;Chivukula, Padmanabh;Karmali, Priya;Tanis, Steven P. US2018/169268, 2018, A1 Location in patent:Paragraph 0024; 0316-0318

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