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17th August 2016 @ 05:11


 NB swopped solvent to diethyl ether as THF column had run dry.


Crude AEW 306-1 (7.42 mmol, 1 equiv.) was dissolved in anydrous diethyl ether (28 mL)  at 0 ˚C. LiAlH4 (4.75 mL, 4.75 mmol, 0.64 equiv.) was added dropwise at 0 ˚C and then allowed to warm to room temperature whilst stirring for x h

The reaction mixture was quenched by the dropwise addition of ice cold water (20 mL) and then extracted into EtOAc (2 x 20 mL). Congregation of aluminium salts/poor separation observed so ammonium chloride solution (5 mL) was added to the aqueous layers and they were quickly re-extracted with EtOAc (20 mL). Combined organic layers were washed with water (10 mL) and then brine (15 mL), dried (MgSO4), filtered and evaporated to yield an orange oil.

The crude residue was purified by flash column chromatography over silica (6:1 Petrol/EtOAc to 100% EtOAc). Four fractions were collected:


20% EtOAc in hexane UV - better visualised in anisaldehyde dip


Hazard and Risk Assessment: