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KlementineJBS / USYD_PhD_ELN

This repository forms the electronic laboratory notebook (ELN)for Klementine Burrell-Sander's PhD's
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KBS30-8 - N-alkylation with KBS29 #178

Closed KlementineJBS closed 7 months ago

KlementineJBS commented 8 months ago

Link to HIRAC and master page.

KBS30 - Generic alkylation of 1,x-diaminoalkane with naphthalene-triazole pendant (updated).docx

Notes

Using NaH as base and THF as solvent.

Reaction scheme

KBS30 alternative nosyl protected

KlementineJBS commented 8 months ago
  1. Added KBS29 (106 mg, 0.369 mmol, 2.9 equiv,) to an oven-dry flask. Much stuck to the sides of the flask and flask cooled considerably during processed
  2. Put under nitrogen
  3. Added NaH (14.5 mg, 60% in mineral oil, 0.363 mmol, 2.8 equiv.)
  4. Evacuated and backfilled x 5
  5. Added KBS43 (63 mg, 0.129 mmol) dissolved in dry THF (4 mL)
  6. Left stirring from 1.40 pm
KlementineJBS commented 8 months ago

LRMS

Signs of SM, no real sign of product.

KBS30-8 RM.pdf KBS30-8 RM.d.zip

KlementineJBS commented 8 months ago

TLC from yesterday (16th) and today.

Definitely signs of some kind of product - unsure why this doesn't show more clearly on MS.

KlementineJBS commented 8 months ago

work up

  1. Quenched with ammonium chloride (10 mL)
  2. Extracted with DCM (3 x 10 mL)
  3. Washed with brine (30 mL)
  4. Dried over mag sulphate and rotovapped down
KlementineJBS commented 8 months ago

LRMS of crude

KBS30-8 cr.pdf KBS30-8 cr.zip