1-(4-fluorophenoxy)-3-methoxypropan-2-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolve 1-(4-fluorophenoxy)-3-methoxy-propan-2-one (860 mg) in ammonia (7N in MeOH, 14.5 mL) and add molecular sieves (1 g). Stir the mixture at ambient temperature overnight. Cool the reaction to 0° C.; add sodium tetrahydroborate (0.66 g, 17.36 mmol); and stir the mixture at ambient temperature for 2 hours. Filter the mixture through a Celite® plug and rinse with MeOH. Concentrate the collected filtrate; dissolve in DCM; and wash with saturated aqueous NaHCO3 solution. Concentrate the filtrate under reduced pressure. Purify the mixture via SCX column, eluting with 7N NH3/MeOH to give the title compound (680 mg, 78.6%). MS (m/z): 200 (M+1). add molecular sieves (1 g) Cool the reaction to 0° C. and stir the mixture at ambient temperature for 2 hours Filter the mixture through a Celite® plug rinse with MeOH Concentrate the collected filtrate dissolve in DCM and wash with saturated aqueous NaHCO3 solution Concentrate the filtrate under reduced pressure Purify the mixture via SCX column eluting with 7N NH3/MeOH

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolve 1-(4-fluorophenoxy)-3-methoxy-propan-2-ol (2.6 g, 12.99 mmol) in DCM (26 mL) and add molecular sieves, pyridinium chlorochromate (7.14 g, 32.47 mmol), and pyridine (5.25 mL, 64.93 mmol). Stir the mixture at ambient temperature overnight. Filter the mixture through a Celite® plug and wash the plug with Et2O. Concentrate the filtrate; then purify via flash column chromatography using 25% EtOAc in hexanes to provide the product as a clear oil (872 mg, 33.9%). MS (m/z): 216 (M+NH4). Filter the mixture through a Celite® plug wash the plug with Et2O Concentrate the filtrate then purify via flash column chromatography