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7-TRIDECANOL synthesis

15synthesis methods
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Yield: 90%

Reaction Conditions:

with sodium tetrahydroborate in tetrahydrofuran;methanol at 0 - 20; for 1 h;

Steps:

7.3 ATX-86: Step 3
To a solution of 44 g tridecane-7-one (1 eq) dissolved in MeOH/THF, 1.5 eq. sodium borohydride was added at 0° C. and the resulting solution was stirred at room temperature for 1 hour. Progress of the reaction was monitored by TLC (10% EtOAc in hexane; Rf: 0.5). Reaction mass was quenched with saturated NH4Cl solution (75 ml). Solvent was removed under reduced pressure and the resulting crude was portioned between EtOAc (150 ml) and water (100 ml). Organic layer was separated and the aqueous layer was washed with EtOAc (3×100 ml). Combined organic layers were concentrated under reduced pressure to get white solid. Quantity produced, 40 g; yield, 90%; 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; 0319-0321

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