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20th October 2011 @ 07:12
Reactions carried out in parallel with MNR11-11/12

MNR12-3%20scheme.png

MNR12-3%20table.PNG

Hazard and Risk Assessment:
As for MNR11-3

Procedure

MNR12-3
MNR10-1(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (5 mg, 0.01 mmol) DCM (2 mL) was heated at reflux.

1st LCMS sample taken after 4 days

After another 24 hours (5 days in total) the reaction was quenched with saturated sodium carbonate and extracted with EtOAc (10 mL x3). The organic fractions were dried over magnesium sulfate, filtered and concentrated under reduced pressure.

Crude - 45 mg

1H NMR MNR12-3

Still large amounts of starting material.

MNR12-4
MNR10-1(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (5 mg, 0.01 mmol) toluene(2 mL) was heated at reflux.

1st LCMS sample taken after 4 days

After another 24 hours (5 days in total) the reaction was quenched with saturated sodium carbonate and extracted with EtOAc (10 mL x3). The organic fractions were dried over magnesium sulfate, filtered and concentrated under reduced pressure.

Crude - 47 mg

1H NMR MNR12-3

Looks a lot better than MNR12-3, -OEt signals from starting material only in trace amounts.

This needs repeated, LCMS shows more SM than product but NMR shows very little SM
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Attached Files
MNR12-3 table.PNG
MNR12-3 scheme.png
mnr12-3.pdf
mnr12-4.pdf