Water → (+/-)2-Hydroxy-5-(p-Toluenesulfonyloxymethyl)-Tetrahydrofuran

Participants

Reaction Conditions

Reaction Steps

To a suspension of (±)-dihydro-5-(p-toluensulfonyloxymethyl)-2(3H)-furanone (example 57) (5.20 g, 19.26 mmol) in anhydrous toluene (125 mL) at -78° C. was added DIBAL (1.5 M in toluene, 13.5 mL, 20.22 mmol) dropwise. The solution was allowed to stir at -78° C. for 2 h. Water was then added to the mixture and the reaction mixture was brought to rt. The mixture was filtered through Celite and the organic layer was collected, dried (MgSO4) and concentrated to give the title compound as a 1:1 mixture of cis and trans isomers (4.2 g, 80%).

Provenance & Evidence