ethyl 2,2-diethoxypropanoate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of ethyl pyruvate diethyl ketal (16.0 g, 0.084 moles) in ethyl ether (60 mL) was added dropwise during 30 min to a stirred solution of lithium aluminum hydride (1.90 g, 0.050 moles) in ethyl ether (150 mL). Next the mixture was stirred 1 h at room temperature under nitrogen atmosphere. Saturated solution of sodium sulfate (20 mL) was added and the mixture was stirred 15 min. Next the mixture was filtered, dried with anhydrous magnesium sulfate, and the solvent was distilled off. The residue was subjected to fractional vacuum distillation giving 9.5 g of pure 2,2-diethoxypropan-1-ol. NMR (d6-DMSO): 1.17 ppm (t, —CH3, ethyl (ketal), 6H), 1.31 ppm (s, —CH3—C—CH2OH, 3H), 3.37 ppm (q, —OCH2CH3, (ketal), 4H), 3.86 ppm (d, —CH2OH, 2H), 4.45 ppm (t, —OH, 1H). the mixture was stirred 15 min Next the mixture was filtered dried with anhydrous magnesium sulfate the solvent was distilled off The residue was subjected to fractional vacuum distillation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of ethyl pyruvate diethyl ketal (16.0 g, 0.084 moles) in ethyl ether (60 mL) was added dropwise during 30 min to a stirred solution of lithium aluminum hydride (1.90 g, 0.050 moles) in ethyl ether (150 mL). Next the mixture was stirred 1 h at room temperature under nitrogen atmosphere. Saturated solution of sodium sulfate (20 mL) was added and the mixture was stirred 15 min. Next the mixture was filtered, dried with anhydrous magnesium sulfate, and the solvent was distilled off. The residue was subjected to fractional vacuum distillation giving 9.5 g of pure 2,2-diethoxypropan-1-ol. NMR (d6-DMSO): 1.17 ppm (t, —CH3, ethyl (ketal), 6H), 1.31 ppm (s, —CH3—C—CH2OH, 3H), 3.37 ppm (q, —OCH2CH3, (ketal), 4H), 3.86 ppm (d, —CH2OH, 2H), 4.45 ppm (t, —OH, 1H). the mixture was stirred 15 min Next the mixture was filtered dried with anhydrous magnesium sulfate the solvent was distilled off The residue was subjected to fractional vacuum distillation

反応条件: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of ethyl pyruvate (13.92 g, 0.120 moles), triethyl orthoformate (19.44 g, 0.131 moles), ethyl alcohol (9.0 g), and p-toluenesulfonic acid monohydrate (0.0432 g, 0.00227 moles) was stirred at 45° C. overnight under nitrogen atmosphere. Next, after cooling to room temperature, Na2CO3 (1.20 g) was added and the mixture was stirred for 15 minutes. The reaction mixture was then filtered and ethyl alcohol and residual triethyl orthoformate were distilled off under reduced pressure. The residue was subjected to fractional vacuum distillation giving 18.2 g of pure ethyl pyruvate diethyl ketal. NMR (d6-DMSO): 1.27 ppm (t, —CH3, ethyl (ketal), 6H) 1.34 ppm (t, —CH3, ethyl (ester), 3H), 1.40 ppm (s, —CH3—C—COO—, 3H), 3.45 ppm (q, —OCH2CH3, (ketal), 4H), 4.29 ppm (q, —OCH2CH3, (ester), 2H). Next, after cooling to room temperature the mixture was stirred for 15 minutes The reaction mixture was then filtered ethyl alcohol and residual triethyl orthoformate were distilled off under reduced pressure The residue was subjected to fractional vacuum distillation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of ethyl pyruvate diethyl ketal (16.0 g, 0.084 moles) in ethyl ether (60 mL) was added dropwise during 30 min to a stirred solution of lithium aluminum hydride (1.90 g, 0.050 moles) in ethyl ether (150 mL). Next the mixture was stirred 1 h at room temperature under nitrogen atmosphere. Saturated solution of sodium sulfate (20 mL) was added and the mixture was stirred 15 min. Next the mixture was filtered, dried with anhydrous magnesium sulfate, and the solvent was distilled off. The residue was subjected to fractional vacuum distillation giving 9.5 g of pure 2,2-diethoxypropan-1-ol. NMR (d6-DMSO): 1.17 ppm (t, —CH3, ethyl (ketal), 6H), 1.31 ppm (s, —CH3—C—CH2OH, 3H), 3.37 ppm (q, —OCH2CH3, (ketal), 4H), 3.86 ppm (d, —CH2OH, 2H), 4.45 ppm (t, —OH, 1H). the mixture was stirred 15 min Next the mixture was filtered dried with anhydrous magnesium sulfate the solvent was distilled off The residue was subjected to fractional vacuum distillation

反応条件: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of ethyl pyruvate (13.92 g, 0.120 moles), triethyl orthoformate (19.44 g, 0.131 moles), ethyl alcohol (9.0 g), and p-toluenesulfonic acid monohydrate (0.0432 g, 0.00227 moles) was stirred at 45° C. overnight under nitrogen atmosphere. Next, after cooling to room temperature, Na2CO3 (1.20 g) was added and the mixture was stirred for 15 minutes. The reaction mixture was then filtered and ethyl alcohol and residual triethyl orthoformate were distilled off under reduced pressure. The residue was subjected to fractional vacuum distillation giving 18.2 g of pure ethyl pyruvate diethyl ketal. NMR (d6-DMSO): 1.27 ppm (t, —CH3, ethyl (ketal), 6H) 1.34 ppm (t, —CH3, ethyl (ester), 3H), 1.40 ppm (s, —CH3—C—COO—, 3H), 3.45 ppm (q, —OCH2CH3, (ketal), 4H), 4.29 ppm (q, —OCH2CH3, (ester), 2H). Next, after cooling to room temperature the mixture was stirred for 15 minutes The reaction mixture was then filtered ethyl alcohol and residual triethyl orthoformate were distilled off under reduced pressure The residue was subjected to fractional vacuum distillation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of ethyl pyruvate diethyl ketal (16.0 g, 0.084 moles) in ethyl ether (60 mL) was added dropwise during 30 min to a stirred solution of lithium aluminum hydride (1.90 g, 0.050 moles) in ethyl ether (150 mL). Next the mixture was stirred 1 h at room temperature under nitrogen atmosphere. Saturated solution of sodium sulfate (20 mL) was added and the mixture was stirred 15 min. Next the mixture was filtered, dried with anhydrous magnesium sulfate, and the solvent was distilled off. The residue was subjected to fractional vacuum distillation giving 9.5 g of pure 2,2-diethoxypropan-1-ol. NMR (d6-DMSO): 1.17 ppm (t, —CH3, ethyl (ketal), 6H), 1.31 ppm (s, —CH3—C—CH2OH, 3H), 3.37 ppm (q, —OCH2CH3, (ketal), 4H), 3.86 ppm (d, —CH2OH, 2H), 4.45 ppm (t, —OH, 1H). the mixture was stirred 15 min Next the mixture was filtered dried with anhydrous magnesium sulfate the solvent was distilled off The residue was subjected to fractional vacuum distillation

反応条件: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of ethyl pyruvate (13.92 g, 0.120 moles), triethyl orthoformate (19.44 g, 0.131 moles), ethyl alcohol (9.0 g), and p-toluenesulfonic acid monohydrate (0.0432 g, 0.00227 moles) was stirred at 45° C. overnight under nitrogen atmosphere. Next, after cooling to room temperature, Na2CO3 (1.20 g) was added and the mixture was stirred for 15 minutes. The reaction mixture was then filtered and ethyl alcohol and residual triethyl orthoformate were distilled off under reduced pressure. The residue was subjected to fractional vacuum distillation giving 18.2 g of pure ethyl pyruvate diethyl ketal. NMR (d6-DMSO): 1.27 ppm (t, —CH3, ethyl (ketal), 6H) 1.34 ppm (t, —CH3, ethyl (ester), 3H), 1.40 ppm (s, —CH3—C—COO—, 3H), 3.45 ppm (q, —OCH2CH3, (ketal), 4H), 4.29 ppm (q, —OCH2CH3, (ester), 2H). Next, after cooling to room temperature the mixture was stirred for 15 minutes The reaction mixture was then filtered ethyl alcohol and residual triethyl orthoformate were distilled off under reduced pressure The residue was subjected to fractional vacuum distillation