Trimethyl orthoformate → HCID 86718424, compound

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).

1. filtrationThe mixture was filtered through glass fiber paper
2. concentrationconcentrated
3. dissolutionThe residue (11.6 g) was dissolved in 60 mL of methanol
4. customequipped with a reflux condenser
5. customdrying tube
6. temperatureThe mixture was heated
7. temperatureat reflux for 70 min
8. temperaturecooled
9. additionpoured into 200 mL of saturated aqueous NaHCO3
10. extractionThe suspension was extracted with 200 mL of CH2Cl2
11. filtrationthe organic was filtered through 1 PS paper
12. concentrationconcentrated at aspirator pressure
13. dissolutionThe 16 g of residue was dissolved in 200 mL of hexanes

ORD record

ord-1582d9815105402292aab75bde36e44e

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729110B1