Acetic Acid → HCID 494700, compound

To a 100 mL round bottomed flask was charged (3aS, 6aR)-3, 3a, 6, 6a-tetrahydro-2H-cyclopenta[b]furan-2-one 49 (3.85 g, 31 mmol, prepared as described in Corey et al. J. Med Chem. 1993, 36, 243), paraformaldehyde (3.0 g), glacial acetic acid (30 mL), and concentrated sulfuric acid (1 mL). The mixture was heated to 74° C. for 24 hours. To the solution was added sodium acetate (4 g). The solution was concentrated in vacuo and the residue was dissolved in ethyl acetate (200 mL). The solution was washed with saturated sodium bicarbonate solution until no gas evolution was observed. The organic phase was dried over sodium sulfate and concentrated in vacuo to give the crude product (4.1 g). The crude product was purified by silica gel column chromatography to provide the title compound (3.1 g, 39%).

1. concentrationThe solution was concentrated in vacuo
2. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
3. washThe solution was washed with saturated sodium bicarbonate solution until no gas evolution
4. dry with materialThe organic phase was dried over sodium sulfate
5. concentrationconcentrated in vacuo
6. customto give the crude product (4.1 g)
7. customThe crude product was purified by silica gel column chromatography

ORD record

ord-cba995dfadf2449dbdf9926330e9be3c

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07034152B2