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KBS17-4 - Propargylation of 1,6-diaminohexane #22
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21.07.22
TLC at 4 pm indicated reaction was not yet complete. (20:80 ethyl acetate:pet benzine) |
22.07.22Mixture had gone black overnight - this seems to indicate that reaction is occurring. TLC at 10 am indicated reaction still not complete. Using 30:70 ethyl acetate: pet benzine gives better resolution of spots. Took off at 4 pm. Diluted with NH4Cl (25 mL) and water (55 mL) then extracted with toluene (4 x 50 mL), washed with water (3 x 125 mL) and brine (150 mL). Dried over MgSO4. |
25.07.22Rotovapped down organic phase. Empty vial: 16.0488 g NMRIndicates more side product than desired product, but uncertain. |
26.07.22LRMS |
26.07.22Ran a manual column - filled with silica slurry (in pet. benz.) to give about ~10 cm silica in a 2.5 cm diameter column. Loaded sample (in pet. benz.) and added fine layer of sand. Added solvent mixture via pipette on sides of column. Solvent system 100 mL 5:95 EtOAc:pet. benz. Collected ~15 mL fractions.
NMRB - fractions 6 - 15 1H NMR (300 MHz, CDCl3) δ 4.01 (4H), 3.29 (4H), 2.17 (2H), 1.55 (4H), 1.46 (18H), 1.30 (4H). KBS17-4 B (F6-15)_1.zip Appears to be reasonably pure desired (bis) product - minor solvent impurities. D - fractions 17 - 20 1H NMR (300 MHz, CDCl3) δ 4.53, 4.01, 3.29, 3.10, 3.08, 2.18, 1.55, 1.46, 1.43, 1.32. KBS17-4 D (17-20)_1.zip Appears to be reasonably pure mono product - minor solvent impurities, particularly ethyl acetate. |
Link to HIRAC, original method and master page.
Last attempt is #19.
Next attempt is #23
KBS17 Generic propargylation of 1,n-diamine.docx
Reaction Scheme
Using 1:5 mixture of DMF:THF as solvent.
Outcome
62% overall
Mono product: 164 mg (0.462 mmol), 36%
Bis product: 129 mg (0.330 mmol), 26%
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