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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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KBS46-1 - N-alkylation with KBS29 and KBS45 #172

Closed KlementineJBS closed 7 months ago

KlementineJBS commented 9 months ago

Link to HIRAC and master page.

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

Reaction scheme

KBS46 alkylation with mono and bis products

KlementineJBS commented 8 months ago
  1. Added 63 mg of SM (0.123 mmol) to a flask
  2. Evacuated and backfilled x 5
  3. Added dry DMF (2 mL) and chilled to 0 C
  4. Added KBS29 (77.0 mg, 0.268 mmol, 2.2 equiv.) dissolved in dry DMF (2 mL)
  5. added cesium carbonate (247 mg, 0.758 mmol, 6 equiv.)
  6. Left stirring from 5.50 pm
KlementineJBS commented 8 months ago

LRMS

1+ peaks: 667.01, 778.90, 854.01 1- peaks: 229.00, 513.10 [M-H]- of SM, 624.24, 712.40

644.94 [M+Cs-2H]- for SM, 646.97 [M+Cs]+ for SM

KBS46-1 RM 11-01-24.pdf KBS46-1 RM 11-01-24.zip

KlementineJBS commented 8 months ago

LRMS

646.95+, 669.28+

512.81- [M-H]- of SM, 594.81-, 626.85-

No sign of either product, only SM.

KBS46-1 RM 12-01-24.d.zip KBS46-1 RM 12-01-24.pdf

KlementineJBS commented 8 months ago

Quenched and worked up today, same as #175. Was much easier/cleaner - not as much thick brown gunk to try and dissolve.

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

TLC at time of quenching:

Solvent system is 4.5% MeOH, 0.5% ammonium hydroxide in DCM

vial: 15.7720 full vial: 15.9218 mass: 140.8 mg (> 100%)

KlementineJBS commented 8 months ago

LRMS

no sign of product.

KBS46-1 cr.d.zip KBS46-1 cr.pdf