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14th February 2012 @ 00:41
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Reaction start time: ~11am 13/02/2012
350 mg (1.5 mmol, 1 equiv.) of PMY 8-4 was dissolved in 3mL chilled toluene under a nitrogen atmosphere. The reaction vessel was cooled in an ice bath whilst thionyl chloride (0.3 mL, 4 mmol, 2.5 equiv.) and 1 drop of DMF as a catalyst were added. The reaction vessel was then raised from the ice bath and the mixture was allowed to react for 3 hr, before the toluene was removed in vacuo.

Paul Ylioja (PMY) took over the experiment from this point, r e-addingtoluene (dried with mol. sieves, 3 mL) and removing it once more in vacuo, before adding hexane (6 mL). The hexane layer, containing the acid chloride, was triturated from the mixture, filtered and concentrated to give a yellow solid (160 mg, xx%). This was dissolved in THF (6 mL).

A day later (16/02/2012, 2:30 pm) I resumed the experiment. Glycolamide (0.025 g, 0.33 mmol), N,N-diisoproylethylamine (0.25 mL, 1.43 mmol) and 4-dimethylaminopyridine (0.0075, 0.06 mmol) were dissolved in dry THF (6 mL) before the yellow acid chloride (80 mg, x mmol, x equiv.) from the previous paragraph was added to the dry reaction vessel under an atmosphere of nitrogen. The reaction mixture was heated to reflux. TLC at 5:45pm showed much starting material remaining, and the reaction was left overnight. The following day had TLC at 1:30pm and 4:15 showed some starting material remaining. Reflux was halted, and the reaction vessel was cooled and left under a nitrogenous atmosphere over the weekend. TLC on Monday morning showed roughly the same amount of starting material remaining. Reaction vessel was removed from nitrogenous atmosphere and the solvent removed in vacuo, before being dissolved in DCM and purified by flash chromatography. Eluent used was EtOAc/petrol in increasing polarity (50%, 70%, 80%, 90%: EtOAc). Suspected product came out using 90%EtOAc/petrol. Solvent was removed to give 28.2 mg (0.09 mmol) in % yield.

TLC: 10%MeOH/DCM, 5:30pm (16/02/2012)
jrc 3-1 (530pm).png


TLC: 10%MeOH/DCM, 1:30pm (17/02/2012)
JRC3-1(midday).JPG


TLC: 10%MeOH/DCM, 4:15pm (17/02/2012)
JRC3-1(4PM).JPG


TLC: 10%MeOH/DCM, 10:00am (20/02/2012)
JRC3-1 20/2/2012 10am


Risk Assessment:
JRC 3-1 RA.docx
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Attached Files
JRC 3-1.png
JRC 3-1 RA.docx
jrc 3-1 (530pm).png
JRC3-1(midday).JPG
JRC3-1(4PM).JPG
JRC3-1 20/2/2012 10am
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