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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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KBS28-8 - Click coupling of 1-azidonaphthalene and propargyl alcohol #161

Closed KlementineJBS closed 7 months ago

KlementineJBS commented 7 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 #153

Reaction scheme

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

Outcome

1.7247 g (7.66 mmol, 94%)

KlementineJBS commented 7 months ago

28.11.23

  1. added CuI (314.6 mg, 0.2 equiv.) and NaAsc (813.6 mg, 0.5 equiv.) to a flask
  2. backfilled with nitrogen x 5
  3. added KBS23 (1.3727 g, 8.12 mmol) dissolved in MeCN (15 mL), propargyl alcohol (0.56 mL, 1.2 equiv.), and DIPEA (2.8 mL, 2 equiv.)
  4. left stirring from 4.45 pm
KlementineJBS commented 7 months ago

29.11.23

TLC indicated reaction was occurring but azide was not yet consumed. Started to heat at 50 C from ~ 3pm.

TLC at 4.30 pm indicated SM was still present. A new spot was visible but this may be due to increased concentration of RM spot.

KlementineJBS commented 7 months ago

30.11.23

Worked up even though SM was still present. Added EDTA (50 mM, 50 mL) and extracted with DCM (3 x 50 mL), then washed with water (2 x 100 mL) and brine (2 x 100 mL).

vial: 15.8128 mass: 1.7247 g (7.66 mmol, 94%)

KlementineJBS commented 7 months ago

H NMR

Looks good. Will carry through without purification. Seems that EDTA wash helps significantly.

KBS28-8 cr.pdf KBS28-8 cr_1.zip