KBS18-1 - Click coupling of azidomethylferrocene and bis-propargyl cyclam

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 1 year ago

KlementineJBS commented 2 years ago

KBS18 reaction scheme

217 mg (0.227 mmol), 91%

KlementineJBS commented 2 years ago

Set up click reaction by adding sodium ascorbate (47.9 mg, 0.242 mmol, 0.88 equiv) and CuSO4.5H2O (26.7 mg, 0.107 mmol, 0.38 equiv.) to a 3-neck flask and evacuating/filling with N2 five times.

NB - equivalents based off cyclam KBS10

Added KBS10 (132 mg, 0.276 mmol) by solution transfer in 2 mL THF
Added KBS16 (112 mg, 0.466 mmol, 1.7 equiv.) by solution transfer in 2 mL THF
Added 3 mL water and stirred at rt from 4.30 pm

KlementineJBS commented 2 years ago

TLC at 2 pm indicated completion (5:95 MeOH:DCM). Reaction was olive green with two layers forming.

THF was removed by rotovapping. The mixture turned a reddish brown colour and started to form a gummy solid.
The reaction was diluted with ammonium chloride buffer (10 mL) to remove excess Cu, and extracted with DCM (3 x 15 mL). During extraction, the organic layer was clearly reddish brown while the aqueous remained olive green.

Organic extracts were dried over MgSO4 and rotovapped down. The initial solution was amber coloured but upon rotovapping the mixture went back to a greenish colour and formed a foam.