Aluminium lithium hydride → HCID 71570849, compound

Participants

Reaction Conditions

Reaction Steps

In a reactor, tetrahydrofuran (110.0 L) was charged under nitrogen, followed by addition of ethyl (1R,7R)-4-phenyl-3,5-dioxabicyclo[5.1.0]octane-1-carboxylate (11.0 kg, 41.9 mol). The mixture was stirred to get a clear solution and cooled to 10-15° C. Lithium aluminium hydride (2 M in tetrahydrofuran, 17.1 L, 35.6 mol) was added drop wise over a period of 1 hour by maintaining the temperature at 10-15° C. The progress of the reaction was monitored by HPLC. After completion of the reaction, the reaction mass was cooled to 0-5° C. and quenched with subsequent addition of ethyl acetate (55.0 L) and brine (55.0 L) maintaining that temperature. The temperature of the reaction mass was gradually raised to 20-25° C. and stirred for 1 h. The organic layer was separated and washed with water (55.0 L) and brine (55.0 L). The organic layer was dried over sodium sulfate (6.0 kg) and the solvent was distilled off. Petroleum ether (22.0 L) was added to the residue to precipitate the product and the slurry was cooled to 0-5° C. and stirred for 30 min. The slurry was filtered and washed with cold petroleum ether (5.0 L). The product was dried in a vacuum tray dryer for 4 hours below 40-45° C. to afford 7.6 Kg of the title compound (5c) as crude product.

Provenance & Evidence