2-(2,3-dimethylphenoxy)ethanol

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

Procedure: A mixture of 5-bromo-3,4-dihydroquinoline-1(2H)-carbonyl chloride (0.05 g, 0.182 mmol), 2-(2,3-dimethylphenoxy)ethanol (0.038 g, 0.228 mmol) and TEA (0.076 mL, 0.546 mmol) in DCM (1.5 mL) was stirred at room temperature for 16 h. To the mixture was then added potassium tert-butoxide (1 M in THF, 0.364 mL, 0.364 mmol) and the resulting mixture was stirred at room temperature for 24 h before being quenched with water. The organic layer was separated and the aqueous phase was extracted with DCM. The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo to provide the crude material. The crude material was purified by flash chromatography (0-50% ethyl acetate/hexanes) to afford the title compound (51 mg, 69.3% yield). LCMS, [M+Na]+=427.9. before being quenched with water The organic layer was separated the aqueous phase was extracted with DCM The combined organic layers were dried over anhydrous MgSO4 concentrated in vacuo to provide the crude material The crude material was purified by flash chromatography (0-50% ethyl acetate/hexanes)

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

Procedure: To a solution of ethyl 2-(2,3-dimethylphenoxy)acetate (1.7 g, 8.16 mmol) in THF (50 mL) at 0° C. was added lithium borohydride (2 M in THF, 8.16 mL, 16.33 mmol) dropwise over a period of 10 min. At the conclusion of this period, the reaction mixture was slowly warmed to room temperature where it stirred for 16 h. After this time, the reaction mixture was quenched slowly with saturated NH4Cl, and the organic layer was separated, washed with water and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to afford the title compound (1.06 g, 78% yield). LCMS, [M+H]+=167.0. After this time, the reaction mixture was quenched slowly with saturated NH4Cl the organic layer was separated washed with water and brine dried over anhydrous MgSO4 filtered concentrated in vacuo