Trimethyl orthoformate → HCID 86718424, compound

Participants

Reaction Steps

2-Dimethoxymethyl-4-ethynylthiophene (15 g, 0.082 mol) was mixed with 1.5 g Pd[C] in 200 mL of methanol and hydrogenated for 4 hr at 44-31 psi. The mixture was filtered through glass fiber paper and concentrated. The residue (11.6 g) was dissolved in 60 mL of methanol and treated with trimethyl orthoformate (19 g, 0.18 mol) and H2SO4 (6 drops) in a flask equipped with a reflux condenser and drying tube. The mixture was heated at reflux for 70 min, cooled, and poured into 200 mL of saturated aqueous NaHCO3. The suspension was extracted with 200 mL of CH2Cl2, and the organic was filtered through 1 PS paper and concentrated at aspirator pressure. The 16 g of residue was dissolved in 200 mL of hexanes and applied to 150 g of silica gel (topped with Na2SO4 and equilibrated with hexanes).

Provenance & Evidence