ethyl 2-(4-hydroxyphenoxy)acetate

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: Ethy 4-benzyloxyphenoxyacetate (21.78 g) was hydrogenated using 7.5% palladium carbon (3.2 g) in tetrahydrofuran (220 ml) at 3 atm over 7 hours. After completion of the reaction, the reaction mixture was filtered through celite, and the solvent was evaporated. The obtained solid was filtrated with diisopropyl ether and dried under reduced pressure to give the title compound (13.88 g) as a white solid. over 7 hours After completion of the reaction the reaction mixture was filtered through celite the solvent was evaporated The obtained solid was filtrated with diisopropyl ether dried under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of hydroquinone(24 g, 0.22 mol) and ethyl bromoacetate(24 mL, 0.22 mol) in DMF(300 mL) was added 10M aq. NaOH(22 mL, 0.22 mol). The mixture was stirred at 0° C. for 1 h, diluted with H2O, acidified with 6M aq. HCl and extracted with EtOAc. The EtOAc extract was dried(anhydrous MgSO4) and concentrated in vacuo. The residue was swished with Et2O to give ethyl 4-hydroxyphenoxy-acetate (5.8 g) as a white powder. extracted with EtOAc The EtOAc extract concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of hydroquinone(24 g, 0.22 mol) and ethyl bromoacetate(24 mL, 0.22 mol) in DMF(300 mL) was added 10 M aq. NaOH(22 mL, 0.22 mol). The mixture was stirred at 0° C. for 1 h, diluted with H2O, acidified with 6M aq. HCl and extracted with EtOAc. The EtOAc extract was dried(anhydrous MgSO4) and concentrated in vacuo. The residue was swished with Et2O to give ethyl 4-hydroxyphenoxy-acetate(5.8 g) as a white powder. extracted with EtOAc The EtOAc extract concentrated in vacuo

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

Procedure: To a 50 mL RB flask fitted with magnetic stirrer was charged 10 mL of Toluene. to the stirred solvent was added ethyl (4-hydroxyphenoxy)acetate (0.2 g, 1.030 mmol) and (4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol (0.22 g, 0.810 mmol) was added Tributyl phosphine (0.268 g, 1.32 mmol) and 1,1′(Azodicarbonyl)di-piperidene (0.33 g, 1.326 mmol). Then the reaction mixture was Stirred at RT for 3 hrs. After completion of the reaction (reaction monitored by TLC), reaction mixture was extracted with ethyl acetate. Then the organic layer was dried over anhydrous Na2SO4. Solvent was removed under reduced pressure, and the resulting crude compound was purified by column chromatography on silica gel using petroleum ether and ethyl acetate as eluent (0.13 g Yield: 28.3%): 1H NMR (300 MHz, CDCl3): δ 7.57-7.60 (m, 2H), 7.18-7.28 (m, 5H), 6.82-6.84 (d, 3H), 6.78-6.79 (d, 3H), 5.12 (s, 2H), 4.83 (s, 2H), 4.49 (s, 2H), 4.15-4.22 (m, 2H), 3.98 (s, 3H), 1.19-1.24 (t, 3H). To a 50 mL RB flask fitted with magnetic stirrer After completion of the reaction (reaction monitored by TLC), reaction mixture was extracted with ethyl acetate Then the organic layer was dried over anhydrous Na2SO4 Solvent was removed under reduced pressure the resulting crude compound was purified by column chromatography on silica gel

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100 mL RB flask fitted with magnetic stirrer was charged 20 mL of DCM to the stirred solvent was added ethyl (4-methoxyphenoxy)acetate (2 g, 9.5 mmol) and Borontribromide (1.85 g, 11.0 mmol) was added at 0° C. Then it was stirred at 0° C. for 30-45 min. After completion of the reaction (reaction monitored by TLC), reaction mass quenched with Sodium bicarbonate and concentrated the reaction mixture and extracted with ethyl acetate. The organic layer was washed with brine and dried by anhydrous Na2SO4 and evaporated to dryness, the resulting crude compound was purified by column chromatography on silica gel using petroleum ether and ethyl acetate as eluent to give the product (0.2 g Yield: 20%): 1H NMR (300 MHz, DMSO-d6): δ 8.97 (s, 1H), 6.72-6.75 (d, 2H), 6.64-6.67 (d, 2H), 4.62 (s, 2H) 4.11-4.18 (q, 2H), 1.18-1.22 (t, 3H). To a 100 mL RB flask fitted with magnetic stirrer was added at 0° C After completion of the reaction (reaction monitored by TLC), reaction mass quenched with Sodium bicarbonate concentrated the reaction mixture extracted with ethyl acetate The organic layer was washed with brine dried by anhydrous Na2SO4 evaporated to dryness the resulting crude compound was purified by column chromatography on silica gel to give the product (0.2 g Yield: 20%)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100 mL RB flask fitted with magnetic stirrer was charged 20 mL of DCM to the stirred solvent was added ethyl (4-methoxyphenoxy)acetate (2 g, 9.5 mmol) and Borontribromide (1.85 g, 11.0 mmol) was added at 0° C. Then it was stirred at 0° C. for 30-45 min. After completion of the reaction (reaction monitored by TLC), reaction mass quenched with Sodium bicarbonate and concentrated the reaction mixture and extracted with ethyl acetate. The organic layer was washed with brine and dried by anhydrous Na2SO4 and evaporated to dryness, the resulting crude compound was purified by column chromatography on silica gel using petroleum ether and ethyl acetate as eluent to give the product (0.2 g Yield: 20%): 1H NMR (300 MHz, DMSO-d6): δ 8.97 (s, 1H), 6.72-6.75 (d, 2H), 6.64-6.67 (d, 2H), 4.62 (s, 2H) 4.11-4.18 (q, 2H), 1.18-1.22 (t, 3H). To a 100 mL RB flask fitted with magnetic stirrer was added at 0° C After completion of the reaction (reaction monitored by TLC), reaction mass quenched with Sodium bicarbonate concentrated the reaction mixture extracted with ethyl acetate The organic layer was washed with brine dried by anhydrous Na2SO4 evaporated to dryness the resulting crude compound was purified by column chromatography on silica gel to give the product (0.2 g Yield: 20%)

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

Procedure: Compound 117 was synthesized from Intermediate 13 (0.22 g, 1.020 mmol) and ethyl (4-hydroxyphenoxy)acetate (0.20 g, 1.020 mmol) by following the procedure described in scheme 41 (0.060 g, yield: 13.72%); Purity: 97.98%.

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

Procedure: Compound 117 was synthesized from Intermediate 13 (0.22 g, 1.020 mmol) and ethyl (4-hydroxyphenoxy)acetate (0.20 g, 1.020 mmol) by following the procedure described in scheme 41 (0.060 g, yield: 13.72%); Purity: 97.98%.

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

Procedure: To a solution of (4-hydroxy-phenoxy)-acetic acid ethyl ester (0.59 g, 3 mmol) in acetic acid (1.5 mL) is added bromine (0.48 g, 9 mmol) in acetic acid (0.5 mL) at room temperature. After 5 min, solvent is evaporated and purified by column chromatography on silica gel giving the title compound (0.6 g). solvent is evaporated purified by column chromatography on silica gel giving the title compound (0.6 g)