1,2-Dimethoxyethane → HCID 86740522, compound

Participants

Reaction Steps

To a slurry of 301.6 mg of 50% sodium hydride in mineral oil and 150 ml of anhydrous dimethoxyethane (DME) is added 1.32 g (5.7 mmole) of 2-oxo-3-methylhept-5-yne dimethylphosphonate (prepared as described in U.S. Pat. No. 4,235,930) in 15 ml of DME at 0° C. under an argon atmosphere. The mixture is stirred at 25° for 1.5 hours. To the solution at 25° is added 1.05 g (3.9 mmole) of [1β,2β(5Z),3α,4β]-7-[3-formyl-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester (prepared as described in Example 1), in 15 ml of DME. After 1 hour the reaction is quenched with 0.7 ml of glacial acetic acid, concentrated, dissolved in 500 ml of ether, washed with three 100 ml portions of 5% NaHCO3 and 100 ml of brine. The organic layer is dried over MgSO4 and concentrated to give 1.66 g of crude title A compound.

Provenance & Evidence