Acetic Acid → HCID 54472112, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of anhydrous CeCl3 (40.5 g, 164 mmol) in THF (500 mL) was refluxed overnight using a Dean Stark trap filled with activated 3 Å molecular sieves. Methyl magnesium chloride (263 mL, 3.0 Molar in THF, 790 mmol) was added dropwise over 30 minutes to the CeCl3 slurry at 0° C. After stirring 2 hours at 0° C., the mixture was cooled to -5° C. and a toluene (600 mL) solution of the hydroxyester (71.8 g, 152 mmol) from Step 5 was added dropwise over 1 hour. The reaction mixture was stirred another hour before the addition of 2M HOAc (600 mL) and toluene (600 mL). The organic layer was washed with saturated aq. NaHCO3 and with brine. Concentration in vacuo and purification of the residue by flash chromatography (30% EtOAc in toluene) gave 63.48 g (91%) of the title compound.

Provenance & Evidence