methyl 2,3-dihydroxypropanoate

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

Procedure: To a solution of methyl glycerate (25.88 g, 215 mmol) and imidazole (22.0 g, 323 mmol, 1.5 eq) in tetrahydrofuran (250 mL) was added t-butyldiphenylsilyl chloride (53.0 mL, 204 mmol, 0.95 eq) at 0° C. After stirring for 18 h the reaction was quenched by the addition of saturated ammonium chloride and the aqueous phase was extracted with dichloromethane. The organic layer was dried with magnesium sulfate and evaporated under reduced pressure. The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20) to give the compound (68.89 g) in 94% yield. was quenched by the addition of saturated ammonium chloride the aqueous phase was extracted with dichloromethane The organic layer was dried with magnesium sulfate evaporated under reduced pressure The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20)

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

Procedure: To a solution of methyl glycerate (25.88 g, 215 mmol) and imidazole (22.0 g, 323 mmol, 1.5 eq) in tetrahydrofuran (250 mL) was added t-butyldiphenylsilyl chloride (53.0 mL, 204 mmol, 0.95 eq) at 0° C. After stirring for 18 h the reaction was quenched by the addition of saturated ammonium chloride and the aqueous phase was extracted with dichloromethane. The organic layer was dried with magnesium sulfate and evaporated under reduced pressure. The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20) to give the compound (68.89 g) in 94% yield. was quenched by the addition of saturated ammonium chloride the aqueous phase was extracted with dichloromethane The organic layer was dried with magnesium sulfate evaporated under reduced pressure The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20)

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

Procedure: To a solution of methyl glycerate (25.88 g, 215 mmol) and imidazole (22.0 g, 323 mmol, 1.5 eq) in tetrahydrofuran (250 mL) was added t-butyldiphenylsilyl chloride (53.0 mL, 204 mmol, 0.95 eq) at 0° C. After stirring for 18 h the reaction was quenched by the addition of saturated ammonium chloride and the aqueous phase was extracted with dichloromethane. The organic layer was dried with magnesium sulfate and evaporated under reduced pressure. The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20) to give the compound (68.89 g) in 94% yield. was quenched by the addition of saturated ammonium chloride the aqueous phase was extracted with dichloromethane The organic layer was dried with magnesium sulfate evaporated under reduced pressure The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20)

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

Procedure: To a solution of methyl glycerate (25.88 g, 215 mmol) and imidazole (22.0 g, 323 mmol, 1.5 eq) in tetrahydrofuran (250 mL) was added t-butyldiphenylsilyl chloride (53.0 mL, 204 mmol, 0.95 eq) at 0° C. After stirring for 18 h the reaction was quenched by the addition of saturated ammonium chloride and the aqueous phase was extracted with dichloromethane. The organic layer was dried with magnesium sulfate and evaporated under reduced pressure. The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20) to give the compound (68.89 g) in 94% yield. 1H NMR (300 MHz, CDCl3) δ: 1.04 (s, 9H, t-butyl), 3.80 (s, 3H, CO2 CH3), 3.93 (dd, 1H, J=2.9 Hz, 9.0 Hz, H-3a), 3.98 (dd, 1H, J=2.9 Hz, 9.0 Hz, H-3b), 4.26 (dd, 1H, J=2.9 Hz, 2.9 Hz, H-2), 7.42 and 7.65 (m, 10H, Ar-H). was quenched by the addition of saturated ammonium chloride the aqueous phase was extracted with dichloromethane The organic layer was dried with magnesium sulfate evaporated under reduced pressure The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20)

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

Procedure: To a solution of methyl glycerate (25.88 g, 215 mmol) and imidazole (22.0 g, 323 mmol, 1.5 eq) in tetrahydrofuran (250 mL) was added t-butyldiphenylsilyl chloride (53.0 mL, 204 mmol, 0.95 eq) at 0° C. After stirring for 18 h the reaction was quenched by the addition of saturated ammonium chloride and the aqueous phase was extracted with dichloromethane. The organic layer was dried with magnesium sulfate and evaporated under reduced pressure. The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20) to give the compound (68.89 g) in 94% yield. was quenched by the addition of saturated ammonium chloride the aqueous phase was extracted with dichloromethane The organic layer was dried with magnesium sulfate evaporated under reduced pressure The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20)

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

Procedure: To a solution of methyl glycerate (25.88 g, 215 mmol) and imidazole (22.0 g, 323 mmol, 1.5 eq) in tetrahydrofuran (250 mL) was added t-butyldiphenylsilyl chloride (53.0 mL, 204 mmol, 0.95 eq) at 0° C. After stirring for 18 h the reaction was quenched by the addition of saturated ammonium chloride and the aqueous phase was extracted with dichloromethane. The organic layer was dried with magnesium sulfate and evaporated under reduced pressure. The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20) to give the compound (68.89 g) in 94% yield. was quenched by the addition of saturated ammonium chloride the aqueous phase was extracted with dichloromethane The organic layer was dried with magnesium sulfate evaporated under reduced pressure The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20)

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

Procedure: A mixture of methyl glycerate (2 g, 0.17 moles) and bromoethanol (5.28 g, 0.42 moles was heated at 60° C. under nitrogen in the presence of a catalytic amount of p-toluene sulfonic acid for 10 h. The excess bromoethanol was removed on rotary evaporator under reduced pressure. The crude mixture was diluted with large volume of chloroform (100 mL) and the free acid was neutralized by adding anhydrous sodium carbonate. Filtration and removal of the solvent gave the crude product which was purified by chromatography on a silica gel column eluting with chloroform:methanol (9:1). Removal of the solvent on a rotary evaporator gave bromoethyl glycerate (3.26 g, 92% yield) which showed the following characteristics: 1H NMR (200 MHz, CDCl3), δ 3.52 (m, 2H, CH2Br), 3.90 (m, 2H,CO2CH2), 4.27 (s, 2H, OH), 4.36 (m, 2H, CH2OH), 4.52 (m, 1H, CH), 13C NMR (50 MHz, CDCl3) δ 28.42, 63.76, 64.50, 71.58, 172.13. The excess bromoethanol was removed on rotary evaporator under reduced pressure The crude mixture was diluted with large volume of chloroform (100 mL) by adding anhydrous sodium carbonate Filtration and removal of the solvent gave the crude product which was purified by chromatography on a silica gel column eluting with chloroform:methanol (9:1) Removal of the solvent on a rotary evaporator

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

Procedure: A mixture of methyl glycerate (2 g, 0.17 moles) and bromoethanol (5.28 g, 0.42 moles was heated at 60° C. under nitrogen in the presence of a catalytic amount of p-toluene sulfonic acid for 10 h. The excess bromoethanol was removed on rotary evaporator under reduced pressure. The crude mixture was diluted with large volume of chloroform (100 mL) and the free acid was neutralized by adding anhydrous sodium carbonate. Filtration and removal of the solvent gave the crude product which was purified by chromatography on a silica gel column eluting with chloroform:methanol (9:1). Removal of the solvent on a rotary evaporator gave bromoethyl glycerate (3.26 g, 92% yield) which showed the following characteristics: 1H NMR (200 MHz, CDCl3), δ 3.52 (m, 2H, CH2Br), 3.90 (m, 2H,CO2CH2), 4.27 (s, 2H, OH), 4.36 (m, 2H, CH2OH), 4.52 (m, 1H, CH), 13C NMR (50 MHz, CDCl3) δ 28.42, 63.76, 64.50, 71.58, 172.13. The excess bromoethanol was removed on rotary evaporator under reduced pressure The crude mixture was diluted with large volume of chloroform (100 mL) by adding anhydrous sodium carbonate Filtration and removal of the solvent gave the crude product which was purified by chromatography on a silica gel column eluting with chloroform:methanol (9:1) Removal of the solvent on a rotary evaporator

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

Procedure: A mixture of methyl glycerate (2 g, 0.17 moles) and bromoethanol (5.28 g, 0.42 moles was heated at 60° C. under nitrogen in the presence of a catalytic amount of p-toluene sulfonic acid for 10 h. The excess bromoethanol was removed on rotary evaporator under reduced pressure. The crude mixture was diluted with large volume of chloroform (100 mL) and the free acid was neutralized by adding anhydrous sodium carbonate. Filtration and removal of the solvent gave the crude product which was purified by chromatography on a silica gel column eluting with chloroform:methanol (9:1). Removal of the solvent on a rotary evaporator gave bromoethyl glycerate (3.26 g, 92% yield) which showed the following characteristics: 1H NMR (200 MHz, CDCl3), δ 3.52 (m, 2H, CH2Br), 3.90 (m, 2H,CO2CH2), 4.27 (s, 2H, OH), 4.36 (m, 2H, CH2OH), 4.52 (m, 1H, CH), 13C NMR (50 MHz, CDCl3) δ 28.42, 63.76, 64.50, 71.58, 172.13. The excess bromoethanol was removed on rotary evaporator under reduced pressure The crude mixture was diluted with large volume of chloroform (100 mL) by adding anhydrous sodium carbonate Filtration and removal of the solvent gave the crude product which was purified by chromatography on a silica gel column eluting with chloroform:methanol (9:1) Removal of the solvent on a rotary evaporator

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

Procedure: A mixture of methyl glycerate (2 g, 0.17 moles) and bromoethanol (5.28 g, 0.42 moles was heated at 60° C. under nitrogen in the presence of a catalytic amount of p-toluene sulfonic acid for 10 h. The excess bromoethanol was removed on rotary evaporator under reduced pressure. The crude mixture was diluted with large volume of chloroform (100 mL) and the free acid was neutralized by adding anhydrous sodium carbonate. Filtration and removal of the solvent gave the crude product which was purified by chromatography on a silica gel column eluting with chloroform:methanol (9:1). Removal of the solvent on a rotary evaporator gave bromoethyl glycerate (3.26 g, 92% yield) which showed the following characteristics: 1H NMR (200 MHz, CDCl3), δ 3.52 (m, 2H, CH2Br), 3.90 (m, 2H,CO2CH2), 4.27 (s, 2H, OH), 4.36 (m, 2H, CH2OH), 4.52 (m, 1 H, CH), 13C NMR (50 MHz, CDCl3) δ 28.42, 63.76, 64.50, 71.58, 172.13. The excess bromoethanol was removed on rotary evaporator under reduced pressure The crude mixture was diluted with large volume of chloroform (100 mL) by adding anhydrous sodium carbonate Filtration and removal of the solvent gave the crude product which was purified by chromatography on a silica gel column eluting with chloroform:methanol (9:1) Removal of the solvent on a rotary evaporator

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

Procedure: To a solution of methyl glycerate (25.88 g, 215 mmol) and imidazole (22.0 g, 323 mmol, 1.5 eq) in tetrahydrofuran (250 mL) was added t-butyldiphenylsilyl chloride (53.0 mL, 204 mmol, 0.95 eq) at 0° C. After stirring for 18 h the reaction was quenched by the addition of saturated ammonium chloride and the aqueous phase was extracted with dichloromethane. The organic layer was dried with magnesium sulfate and evaporated under reduced pressure. The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20) to give the compound (68.89 g) in 94% yield. was quenched by the addition of saturated ammonium chloride the aqueous phase was extracted with dichloromethane The organic layer was dried with magnesium sulfate evaporated under reduced pressure The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20)

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

Procedure: To a solution of methyl glycerate (25.88 g, 215 mmol) and imidazole (22.0 g, 323 mmol, 1.5 eq) in tetrahydrofuran (250 mL) was added t-butyldiphenylsilyl chloride (53.0 mL, 204 mmol, 0.95 eq) at 0° C. After stirring for 18 h the reaction was quenched by the addition of saturated ammonium chloride and the aqueous phase was extracted with dichloromethane. The organic layer was dried with magnesium sulfate and evaporated under reduced pressure. The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20) to give the compound (68.89 g) in 94% yield. was quenched by the addition of saturated ammonium chloride the aqueous phase was extracted with dichloromethane The organic layer was dried with magnesium sulfate evaporated under reduced pressure The crude material was purified by flash chromatography with a mixture of hexanes and ethyl acetate (80:20)