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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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KBS17-12 - Propargylation of 1,6-diaminohexane #52

Closed KlementineJBS closed 10 months ago

KlementineJBS commented 1 year ago

Link to HIRAC, original method and master page.

Last attempt is #51.

KBS17 Generic propargylation of 1,n-diamine.docx

KBS17 hexadiamine

KlementineJBS commented 1 year ago

Method

  1. Dried 10 mL of solvent over 3 A sieves for minimum of 48 hours.
  2. Added ~ 63 mg NaH (1.58 mmol, 5 equiv.) to a dried vial.
  3. Added ~ 100 mg KBS3 (0.316 mmol) dissolved in 3 mL dried solvent.
  4. Left for ~ 6 hours to "activate" (deprotonate)
  1. Added propargyl bromide (0.1 mL, 1.06 mmol, 3.3 equiv.)
  2. Left stirring at rt for 24 hours
  3. Quenched with NH4Cl (3-5 mL)
KlementineJBS commented 1 year ago

20.12.22

LCMS results

Code Solvent pdf Present? Ratio %
A DMF KBS-17-12-A_2-A,8_1_696.pdf SM, mono, bis 11: 100 :28 8:72:20
B 1,4-dioxane KBS-17-12-B_2-B,1_1_697.pdf SM 100 100
C MeCN KBS-17-12-C_2-B,2_1_698.pdf SM, mono, bis 59: 100 : 82 25:41:34
D THF KBS-17-12-D_2-B,3_1_699.pdf SM, mono, bis 76: 100 :18 39:52:9
E DCM KBS-17-12-E_2-B,4_1_700.pdf SM 100:6:5 90:5:5

Notes

Low result for DCM may be due to solvent evaporating before reaction could progress sufficiently. May be worth redoing, but only if MeCN proves a poor choice.

MeCN had highest conversion to desired bis product, but DMF had higher overall conversion (i.e. to either mono or bis product). Future work should investigate using MeCN as a solvent. Perks of MeCN include that it is easier to dry/keep dry than DMF.