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24th August 2012 @ 07:24
Mnr: 11-20
*Duplicate lab book entry to allow data upload

Original post - TfOH catalysed PS* reactions to give the dimethoxy PZQ analogues (KAB8-14 & KAB1-5)

Acetal MNR10 (0.300 g, 0.66 mmol) was dissolved in toluene (30 mL) at room temperature. TfOH (2.92 μL, 0.03 mmol) was added and the reaction was heated to reflux for 3.5 hours. The reaction mixture was allowed to cool to room temperature and diluted with EtOAc (50 mL) then quenched with saturated sodium bicarbonate solution (50 mL), the organic layer was separated and the aqueous fraction was extracted with EtOAc (3 × 30 mL). The organic layers were combined, dried over magnesium sulfate and filtered to give the crude as an orange semi-solid which was recrystallised from EtOAc/Hexane to give the KAB8 as an off white solid (0.211 g, 0.567 mmol, 87 %)

Characterisation

kab08-16_1H.pdf
kab8-16.zip



1H NMR (500 MHz, CDCl3): d = 7.56-7.39 (m, 5H), 6.81 (br, 1H), 6.65 (s, 1H), 5.20 (br, 1H), 4.98-4.75 (m, 2H), 4.34 (br, 1H), 4.17-4.02 (m, 1H), 3.87 (br, 6H), 3.06 (br, 1H), 2.97-2.79 (m, 2H), 2.73-2.64 (m, 1H).

kab08-16_13C.pdf
kab8-16.zip


13C NMR (125 MHz, CDCl3): d = 170.3, 164.2, 148.4, 148.1, 134.2, 130.7, 128.7, 127.4, 127.1, 124.4, 111.8, 108.2, 56.2, 55.9, 54.5, 51.4, 46.1, 39.1, 28.3.


*lab book page closed, MNR
Attached Files
kab8-16.zip
kab08-16_1H.pdf
kab08-16_13C.pdf