KlementineJBS / USYD_PhD_ELN

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

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KBS28-9 - Click coupling of 1-azidonaphthalene and propargyl alcohol #182

Closed KlementineJBS closed 4 months ago

KlementineJBS commented 5 months ago

Link to HIRAC and master page #170. Original method can be found in J. Batten's PhD thesis (2022).

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

Reaction scheme

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

Outcome

870.9 mg (3.87 mmol, 66%)

KlementineJBS commented 4 months ago

31.01.24

added CuI (233 mg, 0.2 equiv.) and NaAsc (587 mg, 0.5 equiv.) to a flask
backfilled with nitrogen x 5
added KBS23 (994 mg, 5.88 mmol) dissolved in MeCN (12 mL), propargyl alcohol (0.4 mL, 1.2 equiv.), and DIPEA (2.06 mL, 2 equiv.)
left stirring overnight

KlementineJBS commented 4 months ago

01.02.24

TLC indicated reaction was occurring if not complete (product spot is near the origin, azide SM is close to top). Used 30% or 40% ethyl acetate in hexanes.

Decided to work up anyway, as in #KBS28-8, as this still had a good yield.

Added EDTA solution (~25 mM, 50 mL)
Extracted with DCM (3 x 50 mL)
Washed with water (2 x 100 mL) and brine (100 mL)
Dried over mag sulphate and rotovapped down

KlementineJBS commented 4 months ago

H NMR (crude)

Looks to contain largely product, with some solvent impurities. Should still column before using in Mitsunobu as material is black and charcoal-like rather than red and gummy or flaky.

KBS28-9 cr_1.zip KBS28-9 cr.pdf

KlementineJBS commented 4 months ago