methyl 2-phenylmethoxyacetate

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: 2-Butanone (47.65 ml) was added dropwise over 10 min to a mechanically stirred suspension of sodium amide (95%; 20.78 g) dry ether (600 ml) at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 15 min. A solution of methyl phenylmethoxyacetate (48.0 g) in dry ether (50 ml) was added dropwise over 13 min at room temperature under nitrogen, and the reaction progressed according to the method of Intermediate 16, to give the title compound as a yellow oil (23.35 g)

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

Procedure: 2-Butanone (47.65 ml) was added dropwise over 10 min to a mechanically stirred suspension of sodium amide (95%; 20.78 g) dry ether (600 ml) at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 15 min. A solution of methyl phenylmethoxyacetate (48.0 g) in dry ether (50 ml) was added dropwise over 13 min at room temperature under nitrogen, and the reaction progressed according to the method of Intermediate 16, to give the title compound as a yellow oil (23.35 g)

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

Procedure: From 2-heptanone and methyl phenylmethoxyacetate according to the method of Intermediate 16.

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

Procedure: From 2-heptanone and methyl phenylmethoxyacetate according to the method of Intermediate 16.

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

Procedure: 2-Hexanone (26.7 g) was added dropwise over 5 min at room temperature to a stirred suspension of sodium amide (10.4 g) in dry ether (290 ml) under nitrogen. The reaction mixture was stirred for 13 min. and a solution of methyl phenylmethoxyacetate (24.0 g) in dry ether (40 ml) was added dropwise over 12 min. The mixture was then heated at reflux for 3 h, cooled, and then poured into ice (400 g) and 2N HC1 (200 ml). The aqueous phase was extracted with ether (2×350 ml) and the combined etheral solution washed with 8% sodium bicarbonate solution (2×250 ml), water (200 ml) and brine (200 ml), then dried and evaporated to leave a yellow liquid (35.8 g). This was purified by column chromatography on silica gel eluting with System A (2:98) to give the title compound as a yellow oil (10.95 g). The mixture was then heated at reflux for 3 h cooled The aqueous phase was extracted with ether (2×350 ml) the combined etheral solution washed with 8% sodium bicarbonate solution (2×250 ml), water (200 ml) and brine (200 ml) dried evaporated

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

Procedure: 2-Hexanone (26.7 g) was added dropwise over 5 min at room temperature to a stirred suspension of sodium amide (10.4 g) in dry ether (290 ml) under nitrogen. The reaction mixture was stirred for 13 min. and a solution of methyl phenylmethoxyacetate (24.0 g) in dry ether (40 ml) was added dropwise over 12 min. The mixture was then heated at reflux for 3 h, cooled, and then poured into ice (400 g) and 2N HC1 (200 ml). The aqueous phase was extracted with ether (2×350 ml) and the combined etheral solution washed with 8% sodium bicarbonate solution (2×250 ml), water (200 ml) and brine (200 ml), then dried and evaporated to leave a yellow liquid (35.8 g). This was purified by column chromatography on silica gel eluting with System A (2:98) to give the title compound as a yellow oil (10.95 g). The mixture was then heated at reflux for 3 h cooled The aqueous phase was extracted with ether (2×350 ml) the combined etheral solution washed with 8% sodium bicarbonate solution (2×250 ml), water (200 ml) and brine (200 ml) dried evaporated

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

Procedure: Benzyloxyacetyl chloride was added slowly to 10 vol of MeOH at 0-5° C. The mixture was stirred at room temperature for 20 h. MeOH was removed under vacuum to give quantitatively the desired product. MeOH was removed under vacuum

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

Procedure: A mixture of 70 (2.75 g, 15.3 mmol) in methanol (50 mL) and hydrazine hydrate (65% in water, 2.3 g, 30 mmol) was heated under reflux for 3 h. The reaction mixture was concentrated under reduced pressure and the residue was diluted with benzene. The solvent was evaporated and the crude product was further dried under high vacuum (6 h) to give 71 (2.75 g), as a light yellow waxy material, which was used in the next step without further purification. was heated under reflux for 3 h The reaction mixture was concentrated under reduced pressure the residue was diluted with benzene The solvent was evaporated the crude product was further dried under high vacuum (6 h)

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

Procedure: A mixture of 70 (2.75 g, 15.3 mmol) in methanol (50 mL) and hydrazine hydrate (65% in water, 2.3 g, 30 mmol) was heated under reflux for 3 h. The reaction mixture was concentrated under reduced pressure and the residue was diluted with benzene. The solvent was evaporated and the crude product was further dried under high vacuum (6 h) to give 71 (2.75 g), as a light yellow waxy material, which was used in the next step without further purification. was heated under reflux for 3 h The reaction mixture was concentrated under reduced pressure the residue was diluted with benzene The solvent was evaporated the crude product was further dried under high vacuum (6 h)

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

Procedure: To a stirred solution of methyl glycolate (2 g, 22.2 mmol) in anhydrous diethyl ether (100 mL), at room temperature, under a nitrogen atmosphere, was added silver(I)oxide (10.3 g, 44.4 mmol). The suspension was stirred for 15 minutes and benzyl bromide (4.5 g, 26.3 mmol) was added. The mixture was stirred at the same temperature for 24 h and the insoluble materials were removed by filtration through a short pad of celite. The filtrate was concentrated under reduced pressure and the crude product chromatographed over a column of silica gel, eluting with 20% diethyl ether-petroleum ether to give 70, as a colorless liquid in 70% yield (2.8 g). The mixture was stirred at the same temperature for 24 h the insoluble materials were removed by filtration through a short pad of celite The filtrate was concentrated under reduced pressure the crude product chromatographed over a column of silica gel eluting with 20% diethyl ether-petroleum ether