Acetone → HCID 13316994, compound

Participants

Reaction Steps

To a solution of the crude mixture of anomers, (4R,6S)-(E)-6-[2-(4'-fluoro-3,3',5-trimethyl[1,1'-biphenyl]-2-yl)ethenyl]-2-ethoxy-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran (0.83 g, 0.0021 mole) in glacial acetic acid (36 ml) was added water (12 ml). Additional acetic acid (3 ml) was added and the solution allowed to stand for 24 hours at which time tlc (silica gel, 5% acetone--CH2Cl2) indicated the reaction was essentially complete. The reaction mixture was poured into water (800 ml) containing sodium hydroxide (50 g) and extracted with ether (1200 ml). After washing the ether extract with water, drying (MgSO4) and evaporating there was obtained crude lactol product (0.68 g). The crude product was purified by flash chromatography (45 mm id column, 4% acetone --CH2Cl2) to give 0.36 g of product which showed a single spot on tlc. 360 MHz H' -NMR in DCCl3 confirmed the presence of two hydroxy anomers in the product.

Provenance & Evidence