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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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KBS21-1 - Propargylation of 1,8-diaminooctane #26

Closed KlementineJBS closed 1 year ago

KlementineJBS commented 1 year ago

Link to HIRAC and master page.

KBS17 Generic propargylation of 1,n-diamine.docx

Reaction Scheme

KBS21 reaction scheme

Outcome

Crude: 355 mg (0.844 mmol), 70%

KlementineJBS commented 1 year ago

01.08.22

  1. Added NaH (407 mg, 17.0 mmol) to a dry flask under nitrogen
  2. Added KBS20 (413.6 mg, 1.20 mmol) by solution transfer (15 mL dry DMF)
  3. Added propargyl bromide (2.84 mmol) and left stirring from 4pm
KlementineJBS commented 1 year ago

02.08.22

TLC at 3 pm indicated some reaction had occurred. Reaction mixture had also turned black, which previously has indicated that reaction is progressing (see #23).

Left stirring a little longer.

KlementineJBS commented 1 year ago

03.08.22

TLC at 12 indicated reaction was still not complete. However, this reaction typically does not go to completion, so the decision was made to work it up anyway.

  1. Diluted with ammonium chloride (15 mL) and water (45 mL)
  2. Extracted with toluene (3 x 40 mL)
  3. Washed with water to remove DMF (3 x 100 mL)
  4. Brine wash (120 mL)
  5. Dried over MgSO4 and rotovapped down
KlementineJBS commented 1 year ago

04.08.22

Empty vial: 15.8923 Full vial: 16.2472 Mass: 354.9 mg

PXL_20220804_015248724 MP

(Crystals formed in RBF when left overnight)

H NMR

1H NMR (300 MHz, CDCl3) δ 4.49, 4.00, 3.29, 3.10, 3.08, 2.18, 1.46, 1.44, 1.29, 1.25.

KBS21-1_1.zip

KBS21-1 cr processed.pdf

Appears to be a mixture of both mono and bis products, as expected. Will confirm with mass spec and likely column manually as with #22.

KlementineJBS commented 1 year ago

05.08.22

KBS21-1 cr.pdf

KlementineJBS commented 1 year ago

08.08.22

Fractions Empty vial Full vial Mass (mg) Moles (mmol) Yield (%) Compound
2 - 5 16.0268 16.1272 - - - -
12 - 14 15.9860 15.9863 - - - -
16 - 20 15.7857 15.7973 11.6 - - -
21 - 24 16.0074 16.0565 49.1 - - -
25 - 27 16.0780 - - - - -
28 15.8620 16.1607 298.7 - - -
KlementineJBS commented 1 year ago

11.08.22

KBS21-1 F21-24.pdf KBS21-1 F28.pdf KBS21-1 F25-27.pdf KBS21-1 F28.d.zip KBS21-1 F21-24.d.zip KBS21-1 F25-27.d.zip