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11th October 2011 @ 00:16
Synthesis of ethyl 2-acetyl-4-oxopentanoate intermediate. Refer to LMW 8-1 and LMW 9-1.

LMW%207-1%20intermediate.png

Experiment Start Time: 10:20 EST 11/10/11
Ethyl acetoacetate (6 mL,47 mmol, 1 equiv.) and K2CO3 (8.45 g, 61.1 mmol, 1.3 equiv.) were mixed in acetonitrile (55 mL). Sodium Iodide (7.05 g, 47 mmol, 1 equiv.) and Chloroacetone (4.8 mL, 51.7 mmol, 1.1 equiv.) were added and mixture heated to 80oC in an oil bath. TLC at 2 hours showed reaction at completion with no sign of starting materials. Reaction was allowed to cool. Reaction mixture was then filtered and washed with EtOAc (20 mL) and concentrated under reduced pressure to form a yellow oil. Mixture was then washed with EtOAc (2 x 20 mL), water (2 x 20 mL), 1:1 water:brine (2 x 20 mL) and brine (2 x 20 mL) and dried with MgSO4 and concentrated under reduced pressure.

TLC (25% EtOAc, petrol) at 1.5 and 2 hrs, Visualised with UV and Vanillin:
TLC 1.5 and 2 hrs reaction time

Left: Ethyl acetoacetate, Centre: Ethyl acetoacetate and reaction mixture, Right: reaction mixture

Hazard and Risk Assessment:
Refer to Synthesis of ethyl 2,5-dimethyl-1-(p-tolyl)-1H-pyrrole-3-carboxylate (LMW 6-1)
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Reaction scheme
TLC 1.5 and 2 hrs reaction time