diethyl 2-[2-(2-methoxyethoxy)ethyl]propanedioate

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

実験手順: Sodium hydroxide (2.00 g, 50.00 mmol) in water (15 mL) was added to a stirred solution of diethyl[2-(2-methoxyethoxy)ethyl]malonate (Step 1) (2.35 g, 8.96 mmol). The reaction was kept at ambient temperature for 10 minutes before MeOH was removed in vacuo. The resulting solution was acidified to pH=1 by the addition of HCl (5 M). Diethyl ether was added and the two phases were separated. The aqueous phase was extracted three times with diethyl ether. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo to give the title compound as a colourless oil (1.81 g), 1H NMR (300 MHz, CDCl3) δ 7.16 (br s, 2H), 3.58 (m, 7H), 3.40 (s, 3H), 2.23 (m, 2H). was removed in vacuo The resulting solution was acidified to pH=1 by the addition of HCl (5 M) Diethyl ether was added the two phases were separated The aqueous phase was extracted three times with diethyl ether dried over MgSO4 concentrated in vacuo

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

実験手順: Sodium (0.72 g, 31.31 mmol) was added in portions to EtOH (99.5%, 35 mL) under stirring. When all sodium had dissolved, diethyl malonate (4.80 g, 29.97 mmol) was added slowly during 5 minutes and the reaction mixture was stirred for another 15 minutes. 1-Bromo-2-(2-methoxyethoxy)-ethane (5.50 g, 30.05 mmol) was added and the reaction mixture was refluxed for 2 hrs. Any solids were filtered off and the clear solution was concentrated in vacuo. The residue was taken up in water and diethyl ether and the two phases were separated. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with EtOAc/MeOH:20/1) to give the title compound as a colourless oil (3.80 g), 1H NMR (300 MHz, CDCl3) δ 4.19 (q, 4H), 3.54 (m, 7H), 3.38 (s, 3H), 2.19 (m, 2H), 1.27 (t, 6H). the reaction mixture was stirred for another 15 minutes the reaction mixture was refluxed for 2 hrs Any solids were filtered off the clear solution was concentrated in vacuo diethyl ether and the two phases were separated The organic phase was dried over MgSO4 concentrated in vacuo The residue was purified with column chromatography (silica gel, eluting with EtOAc/MeOH:20/1)

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

実験手順: Sodium hydroxide (2.00 g, 50.00 mmol) in water (15 mL) was added to a stirred solution of diethyl[2-(2-methoxyethoxy)ethyl]malonate (Step 1) (2.35 g, 8.96 mmol). The reaction was kept at ambient temperature for 10 minutes before MeOH was removed in vacuo. The resulting solution was acidified to pH=1 by the addition of HCl (5 M). Diethyl ether was added and the two phases were separated. The aqueous phase was extracted three times with diethyl ether. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo to give the title compound as a colourless oil (1.81 g), 1H NMR (300 MHz, CDCl3) δ 7.16 (br s, 2H), 3.58 (m, 7H), 3.40 (s, 3H), 2.23 (m, 2H). was removed in vacuo The resulting solution was acidified to pH=1 by the addition of HCl (5 M) Diethyl ether was added the two phases were separated The aqueous phase was extracted three times with diethyl ether dried over MgSO4 concentrated in vacuo

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

実験手順: Sodium (0.72 g, 31.31 mmol) was added in portions to EtOH (99.5%, 35 mL) under stirring. When all sodium had dissolved, diethyl malonate (4.80 g, 29.97 mmol) was added slowly during 5 minutes and the reaction mixture was stirred for another 15 minutes. 1-Bromo-2-(2-methoxyethoxy)-ethane (5.50 g, 30.05 mmol) was added and the reaction mixture was refluxed for 2 hrs. Any solids were filtered off and the clear solution was concentrated in vacuo. The residue was taken up in water and diethyl ether and the two phases were separated. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with EtOAc/MeOH:20/1) to give the title compound as a colourless oil (3.80 g), 1H NMR (300 MHz, CDCl3) δ 4.19 (q, 4H), 3.54 (m, 7H), 3.38 (s, 3H), 2.19 (m, 2H), 1.27 (t, 6H). the reaction mixture was stirred for another 15 minutes the reaction mixture was refluxed for 2 hrs Any solids were filtered off the clear solution was concentrated in vacuo diethyl ether and the two phases were separated The organic phase was dried over MgSO4 concentrated in vacuo The residue was purified with column chromatography (silica gel, eluting with EtOAc/MeOH:20/1)