Sodium borohydride → (5-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorophenyl)methanol

Participants

Reaction Steps

Sodium borohydride (1.33 g) was added portionwise over 30 minutes to a solution at 0° C. of 5-(2-(tert-butyldimethylsilyloxy)ethyl)-2-fluorobenzaldehyde [Aromatic Intermediate 3, step b] (9.9 g) in ethanol (120 mL). The reaction mixture was then stirred at room temperature for 30 minutes before being reduced to half the initial volume by concentration under reduced pressure. The residue was partitioned between ethyl acetate and brine, the organic layer was washed with brine, dried, filtered and the solvent concentrated under reduced pressure. The crude product was purified by flash silica chromatography using 12% ethyl acetate in isohexane as solvent. Fractions containing the product were concentrated to dryness to afford the titled compound. Yield 7.30 g.

Provenance & Evidence