KlementineJBS / USYD_PhD_ELN

This repository forms the electronic laboratory notebook (ELN)for Klementine Burrell-Sander's PhD's

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Closed KlementineJBS closed 4 months ago

KlementineJBS commented 5 months ago

Previous attempt is #165

Notes

Using cesium carbonate as base.

KBS30 alternative nosyl protected

KlementineJBS commented 5 months ago

Added 58 mg of SM (0.120 mmol) to a flask
Evacuated and backfilled x 5
Added dry DMF (2 mL) and chilled to 0 C
Added KBS29 (77.2 mg, 0.269 mmol, 2.2 equiv.) dissolved in dry DMF (2 mL) and cesium carbonate (233.4 mg, 0.716 mmol, 6 equiv.). Technically added extra cesium carbonate as first amount measured out had largely absorbed water and was tossed, but some remaining dry powder got into flask.
Left stirring at rt from 2.50 pm

KlementineJBS commented 5 months ago

SM is evident. Mono product briefly glimpsed but not clearly evident. Some mystery peaks.

Mystery 1+ peaks: 309.24, 602.08, 750.80 Mystery 1- peaks: 564.95

618.94 [M+Cs]+ of SM, 617.00 [M+Cs-2H]- of SM

KlementineJBS commented 5 months ago

After two days reaction time, being heated to 50 C for one of those days, decided to work up.
Quenched with ammonium chloride solution (10 mL)
Extracted with toluene (3 x 20 mL) and small amount of DCM.
Washed with LiCl solution (5%, 2 x 40 mL), water (2 x 40 mL) and brine (40 mL)
Dried over mag sulphate and rotovapped down.

TLC at time of quenching: