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 10 months ago

KlementineJBS commented 12 months ago

Reaction scheme

Need to do under nitrogen!

KBS36 - Synthesis of 1-(5-phenylpyridin-2-yl)ethan-1-one

KlementineJBS commented 11 months ago

Added the following to a 25 mL 2-neck flask: phenylboronic acid (263 mg, 2.16 mmol, 1.2 equiv.), 2-acetyl-5-bromopyridine (350 mg, 1.75 mmol), potassium carbonate (483 mg, 3.49 mmol, 2 equiv.) and Pd(Ph3)4 (10 mg, 0.008 mmol)
Evacuated and backfilled flask x 5
Added toluene (10 mL) and water (2 mL)
Swapped out to a condenser
Heated to 105 C from 1.30 pm

Discovered at 4 pm that reaction had gone dry. Added the same solvents again. TLC indicated no reaction.

KlementineJBS commented 11 months ago

TLC at 10 am indicated reaction was progressing but incomplete. Lots of yellow precipitate was present on the edge of the flask.

TLC'd again at 5 pm. Looked similar. Topped up solvents (1 mL water, 5 mL toluene) and left overnight.

Eluent is 10% ethyl acetate in hexanes

KlementineJBS commented 11 months ago

KlementineJBS commented 11 months ago

Indicates that product was formed (methyl peak at 2.79) but some starting material remains (methyl peak at 2.70). See literature reference.

KlementineJBS commented 10 months ago

Empty vial: 15.8813 Full vial: 16.2188 Mass: 337.5 mg, of which 287.6 mg is calculated to be product

Appears to be approximately 85% conversion rate, giving a yield of 83%.

KlementineJBS commented 10 months ago

Peak at 220.11 [M+Na]+ confirms that fractions 10+ are probably product.

KlementineJBS commented 10 months ago

NMR of column fractions indicates that fractions 7-9 and 10+ are product. (SM peak at 2.68, product at 2.78)