Ethyl 2-(4-hydroxyphenyl)-2-oxoacetate

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:

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: 7.25 g of ethyl 2-(4-hydroxyphenyl)-2-oxoacetate was dissolved in 15 ml of pyridine, followed by adding 4 ml of acetic anhydride and then stirring at room temperature for 1 hour. The resulting reaction solution was poured into water, and extracted with diethyl ether. The resulting organic layer was washed with water, and then concentrated to dryness. Thereafter, the residue was dissolved in benzene, and then concentrated to obtain 8.3 g of the title compound in an oily form. The resulting reaction solution extracted with diethyl ether The resulting organic layer was washed with water concentrated to dryness Thereafter, the residue was dissolved in benzene concentrated

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

Procedure: To 40 ml of tetrahydrofuran were dissolved 1.8 g of ethyl 2-(4-hydroxyphenyl)-2-oxoacetate, 1.74 g of (3R)-1-tert-butoxycarbonyl-3-hydroxypyrrolidine and 2.92 g of triphenylphosphine. At room temperature, 1.94 g of diethyl azodicarboxylate was added to the above solution, and the resulting mixture was stirred for 18 hours. After distilling off the solvent, the residue thus obtained was dissolved in ethyl acetate, and the solution was washed with water, and then dried. Thereafter, the solvent was distilled-off, and the resulting residue was purified by silica gel column chromatography using a toluene/chloroform mixture as an eluant, thereby obtaining 2.53 g of the title compound as a viscous yellow oil. After distilling off the solvent the residue thus obtained the solution was washed with water dried the resulting residue was purified by silica gel column chromatography

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

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

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.62 g (8.39 mmol) ethyl 4-hydroxybenzoylformate and 5.79 g (42 mmol) K2CO3 are dissolved in 70 ml acetone. 1.22 g (10.1 mmol) allyl bromide is added dropwise at room temperature. The mixture is heated at 40° C. for 3.25 hours under nitrogen atmosphere. The mixture is then filtered and evaporated. The phases are separated and water is extracted with toluene. The organic phases are dried over magnesium sulfate. Evaporation of the solvent and chromatography (eluent: hexane ethyl acetate 3:1) give 1.39 g (71 wt %) of a yellow oil. The mixture is then filtered evaporated The phases are separated water is extracted with toluene The organic phases are dried over magnesium sulfate Evaporation of the solvent and chromatography (eluent: hexane ethyl acetate 3:1) give 1.39 g (71 wt %) of a yellow oil

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

Procedure: 15.3 g of chromium trioxide is added dropwise to a solution of 15 g of ethyl 4-hydroxymandelate in 240 ml of acetic acid. The mixture is stirred at room temperature for 2 hours, poured into 1 l of ethyl acetate and extracted with saturated aqueous Na2CO3 solution. The aqueous phases are extracted with methylene chloride. The organic phases are washed with saturated aqueous Na2CO3 solution, followed by washing with water. The organic phases are dried over sodium sulfate. Filtration, evaporation of the solvent and distillation (ball-tube still distillation, boiling point 205° C. (0.076 bar)) give 4.04 g (27 wt %) ethyl 4-hydroxybenzoylformate as a yellow solid. extracted with saturated aqueous Na2CO3 solution The aqueous phases are extracted with methylene chloride The organic phases are washed with saturated aqueous Na2CO3 solution by washing with water The organic phases are dried over sodium sulfate Filtration, evaporation of the solvent and distillation (ball-tube still distillation, boiling point 205° C. (0.076 bar))