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

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

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 2-(4-fluorophenoxy)propane-1,3-diol (186 mg, 0.99 mmol) in THF (5 mL), and add sodium hydride (60% dispersion in mineral oil, 24 mg, 1 mmol). Stir the mixture for 30 minutes at ambient temperature then add iodomethane (0.4 mL, 4.09 mmol). Stir the reaction at ambient temperature for 16 hours. Remove the solvents under reduced pressure and add water to the residue. Extract with EtOAc three times; collect the EtOAc extracts; dry; and remove the solvents under reduced pressure. Purify the residue via prep-TLC using 1:1 EtOAc:petroleum ether, to give the title compound (50 mg, 31.0%). 1H NMR (300 MHz, CDCl3) δ 7.0 (m, 4H), 4.2-4.5 (m, 2H), 3.8 (m, 2H), 3.55 (m, 1H), 3.35 (m, 2H), 2.35 (bs, 1H), 2.0 (s, 3H). Stir the reaction at ambient temperature for 16 hours Remove the solvents under reduced pressure add water to the residue Extract with EtOAc three times collect the EtOAc dry and remove the solvents under reduced pressure Purify the residue