Tetrabutylammonium Fluoride → (R)-2-Hydroxymethyl-8-methoxy-chroman

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl(dimethyl)silyl [(2R)-8-methoxy-3,4-dihydro-2H-chromen-2-yl]methyl ether (4.50 g, 14.6 mmol) in tetrahydrofuran (150 mL) at 0° C. is added excess tetrabutylammonium fluoride (1.0 M in tetrahydrofuran) and the reaction mixture is allowed to stir at 22° C. for 30 min. The solvent is removed in vacuo and the residue is purified by flash column chromatography (silica, ethyl acetate:hexanes 1:1) to give 2.49 g (88%, 40% ee) of [(2R)-8-methoxy-3,4-dihydro-2H-chromen-2-yl]methanol as a white crystalline solid.

Provenance & Evidence