KlementineJBS / USYD_PhD_ELN

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

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KBS28-6 - Click coupling of 1-azido-naphthyl and propargyl alcohol #151

Closed KlementineJBS closed 7 months ago

KlementineJBS commented 8 months ago

Link to HIRAC and master page. Original method can be found in J. Batten's PhD thesis (2022).

KBS28 - Click coupling with 1-azidonaphthalene and propargyl alcohol.docx

Previous attempt is #150

Using 2 equivalents of DIPEA and 1.2 equivalents propargyl alcohol. Will add extra propargyl alcohol (1.2 equiv.) if not done after reacting overnight. Next step is to try heating.

Reaction scheme

KBS28 alternative - Click coupling of 1-azidonaphthalene and propargyl alcohol

Outcome

KlementineJBS commented 8 months ago

Added NaAsc (287.5 mg 1.45 mmol, 0.5 equiv.) and CuI (114.3 mg, 0.600 mmol, 0.2 equiv.) to a flask
Backfilled with N2 x 5
Added DIPEA (1.01 mL, 5.8 mmol, 2 equiv.)
Added propargyl alcohol (0.18 mL, 3.19 mmol, 1.1 equiv.) and 1-azidonapthyl (491 mg, 2.90 mmol) dissolved in MeCN (8 mL)
left stirring at rt from 4.30 pm

KlementineJBS commented 8 months ago

Reaction not yet complete at 12 pm. Solution was bright carrot orange so added 282.2 mg NaAsc (1.45 mmo, 0.5 equiv.) and 1-2 mL MeCN.

KlementineJBS commented 8 months ago

SM still evident by TLC at 9 am.

KlementineJBS commented 8 months ago

30.10.23

Had to turn reaction off over the weekend due to shutdown. Turned back on to stirring (no heating) around 11 am and reaction was complete by 2 pm.

Added some water (20 mL) and worked up with DCM (4 x 20 mL). Washed with water (20 mL) and brine (20 mL), which helped a lot with emulsions. Maybe should do 2 x brine wash next time?