Methyl Acetate → HCID 131717673, compound

Participants

Reaction Steps

1.02 g (8.8 mmol) of methyl acetate in 5 ml of dry tetrahydrofuran are added dropwise under nitrogen to a suspension of 330 mg (11 mmol) of 80% strength sodium hydride in 30 ml of dry tetrahydrofuran at -5° C. After 15 min, 5.5 ml (8.8 mmol) of 15% strength butyllithium in n-hexane ere added dropwise at the same temperature and the mixture is stirred for 15 minutes. Subsequently, 2 g (4.4 mmol) of the compound from Example 8 dissolved in 20 ml of dry tetrahydrofuran are added dropwise and the mixture is stirred for 30 minutes at -5° C. 3 ml of 50% strength acetic acid are cautiously added to the reaction solution, and the mixture is diluted using 100 ml of water and extracted three times using 100 ml of ether each time. The combined organic phases are washed twice with saturated sodium hydrogen carbonate solution and once with saturated sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo. The residue is chromatographed on a column (100 g of silica gel 70-230 mesh, φ3 cm, using ethyl acetate/petroleum ether 3:7).

Provenance & Evidence