Tetrabutylammonium Fluoride → (R)-Methyl 5-(3-(3-(hydroxymethyl)-1,1-dioxidoisothiazolidin-2-yl)-propyl)-thiophene-2-carboxylate

Participants

Reaction Steps

Tetrabutylammonium fluoride (1.95 mL of a 1.0M solution in THF, 1.95 mmol) was added to a solution of the silyl ether 9 (751 mg, 1.29 mmol) in THF (3.0 mL). After stirring for 16 h the reaction was diluted with EtOAc and washed with water followed by brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 20% EtOAc/hex followed by 40% EtOAc/hex) afforded 317 mg (73%) of alcohol 10.

Provenance & Evidence