ethyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate

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

実験手順: 2,2-bis(methylol)propionic acid (bis-MPA) (22.1 g, 0.165 mol) was added in ethanol (150 mL) with Amberlyst-15 (6.8 g) and refluxed overnight. The resins were then filtered out and the filtrate was evaporated. Methylene chloride (200 mL) was added to the resulting viscous liquid to filter the unreacted reagent and by-products. The solution was dried over Mg504, filtered, and the solvent was removed in vacuo. Ethyl 2,2-bis(methylol)propionate was obtained as a clear and colorless liquid (21.1 g, 86% yield). refluxed overnight The resins were then filtered out the filtrate was evaporated Methylene chloride (200 mL) was added to the resulting viscous liquid to filter the unreacted reagent and by-products The solution was dried over Mg504 filtered the solvent was removed in vacuo

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

実験手順: A solution of triphosgene (19.5 g, 0.065 mol) in CH2Cl2 (200 mL) was added stepwise to a CH2Cl2 solution (150 mL) of ethyl 2,2-bis(methylol)propionate (EtMPA) (21.1 g, 0.131 mol) and pyridine (64 mL, 0.786 mol) over 30 min at −75° C. with dry ice/acetone. The reaction mixture was kept stirring for another 2 hours under chilled condition and then allowed to heat to room temperature. Saturated NH4Cl aqueous solution (200 mL) was added to the reaction mixture to decompose excess triphosgene. The organic phase was then treated with 1 N HCl aq (200 mL), followed by saturated NaHCO3 (200 mL), brine (200 mL), and water (200 mL). After the CH2Cl2 solution was dried over MgSO4 and evaporated, the residue was recrystallized from ethyl acetate to give white crystals (13.8 g, 56%). 1H NMR: delta 4.68 (d, 2H, CH2OCOO), 4.25 (q, 1H, OCH2CH3), 4.19 (d, 2H, CH2OCOO), 1.32 (s, 3H, CH3), 1.29 (t, 3H, CH3CH2O). 13C NMR: delta 171.0, 147.5, 72.9, 62.1, 39.9, 17.3, 13.8. HR-ESI-MS: m/z calcd for C8H12O5; Na, 211.0582; found, 221.0578. under chilled condition After the CH2Cl2 solution was dried over MgSO4 evaporated the residue was recrystallized from ethyl acetate

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

実験手順: 2,2-Bis(methylol)propionic acid (bisMPA; molecular weight 134.1, 22.1 g, 0.165 mol) was added in ethanol (150 mL) with Amberlyst-15 (6.8 g) and refluxed overnight. The resins were then filtered out and the filtrate was evaporated. Methylene chloride (200 mL) was added to the resulting viscous liquid to filtrate the unreacted reagent and byproduct. After the solution was dried over MgSO4 and evaporated, ethyl 2,2-bis(methylol)propionate (EtMPA) was obtained as a clear and colorless liquid (21.1 g, 86%). refluxed overnight The resins were then filtered out the filtrate was evaporated Methylene chloride (200 mL) was added to the resulting viscous liquid to filtrate the unreacted reagent and byproduct After the solution was dried over MgSO4 evaporated

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

実験手順: 2,2-bis(methylol)propionic acid (bis-MPA) (22.1 g, 0.165 mol) was added in ethanol (150 mL) with Amberlyst-15 (6.8 g) and refluxed overnight. The resins were then filtered out and the filtrate was evaporated. Methylene chloride (200 mL) was added to the resulting viscous liquid to filter the unreacted reagent and by-products. The solution was dried over Mg504, filtered, and the solvent was removed in vacuo. Ethyl 2,2-bis(methylol)propionate was obtained as a clear and colorless liquid (21.1 g, 86% yield). refluxed overnight The resins were then filtered out the filtrate was evaporated Methylene chloride (200 mL) was added to the resulting viscous liquid to filter the unreacted reagent and by-products The solution was dried over Mg504 filtered the solvent was removed in vacuo

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

実験手順: 2,2-bis(methylol)propionic acid (bis-MPA) (22.1 g, 0.165 mol) was added in ethanol (150 mL) with Amberlyst-15 (6.8 g) and refluxed overnight. The resins were then filtered out and the filtrate was evaporated. Methylene chloride (200 mL) was added to the resulting viscous liquid to filter the unreacted reagent and by-products. The solution was dried over Mg504, filtered, and the solvent was removed in vacuo. Ethyl 2,2-bis(methylol)propionate was obtained as a clear and colorless liquid (21.1 g, 86% yield). refluxed overnight The resins were then filtered out the filtrate was evaporated Methylene chloride (200 mL) was added to the resulting viscous liquid to filter the unreacted reagent and by-products The solution was dried over Mg504 filtered the solvent was removed in vacuo

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

実験手順: 2,2-bis(methylol)propionic acid (bis-MPA) (22.1 g, 0.165 mol) was added in ethanol (150 mL) with Amberlyst-15 (6.8 g) and refluxed overnight. The resins were then filtered out and the filtrate was evaporated. Methylene chloride (200 mL) was added to the resulting viscous liquid to filter the unreacted reagent and by-products. The solution was dried over MgSO4, filtered, and the solvent was removed in vacuo. Ethyl 2,2-bis(methylol)propionate was obtained as a clear and colorless liquid (21.1 g, 86% yield). refluxed overnight The resins were then filtered out the filtrate was evaporated Methylene chloride (200 mL) was added to the resulting viscous liquid to filter the unreacted reagent and by-products The solution was dried over MgSO4 filtered the solvent was removed in vacuo

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

実験手順: 2,2-Bis(methylol)propionic acid (bis-MPA; MW 134.1, 22.1 g, 0.165 mol) was added in ethanol (150 mL) with Amberlyst-15 (6.8 g) and refluxed overnight. The resins were then filtered out and the filtrate was evaporated. Methylene chloride (200 mL) was added to the resulting viscous liquid to filtrate the unreacted reagent and byproduct. After the solution was dried over MgSO4 and evaporated, ethyl 2,2-bis(methylol)propionate (EtMPA) was obtained as a clear and colorless liquid (21.1 g, 86%). refluxed overnight The resins were then filtered out the filtrate was evaporated Methylene chloride (200 mL) was added to the resulting viscous liquid to filtrate the unreacted reagent and byproduct After the solution was dried over MgSO4 evaporated

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

実験手順: A solution of triphosgene (19.5 g, 0.065 mol) in CH2Cl2 (200 mL) was added stepwise to a CH2Cl2 solution (150 mL) of ethyl 2,2-bis(methylol)propionate (MPAEt) (21.1 g, 0.131 mol) and pyridine (64 mL, 0.786 mol) over 30 min at −75° C. with dry ice/acetone. The reaction mixture was kept stirring for another 2 hours under chilled condition and then allowed to heat to room temperature. Saturated NH4Cl aqueous solution (200 mL) was added to the reaction mixture to decompose excess triphosgene. The organic phase was then treated with 1 N HCl aq (200 mL), followed by saturated NaHCO3 (200 mL), brine (200 mL), and water (200 mL). After the CH2Cl2 solution was dried over MgSO4 and evaporated, the residue was recrystallized from ethylacetate to give white crystals (13.8 g, 56%). 1H NMR: delta 4.68 (d, 2H, CH2OCOO), 4.25 (q, 1H, OCH2CH3), 4.19 (d, 2H, CH2OCOO), 1.32 (s, 3H, CH3), 1.29 (t, 3H, CH3CH2O). 13C NMR: delta 171.0, 147.5, 72.9, 62.1, 39.9, 17.3, 13.8. HR-ESI-MS: m/z calcd for C8H12O5.Na, 211.0582; found, 221.0578. under chilled condition After the CH2Cl2 solution was dried over MgSO4 evaporated the residue was recrystallized from ethylacetate

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

実験手順: 2,2-Bis(methylol)propionic acid (bisMPA; 22.1 g, 0.165 mol) was added in ethanol (150 mL) with Amberlyst-15 (6.8 g) and refluxed overnight. The resins were then filtered out and the filtrate was evaporated. Methylene chloride (200 mL) was added to the resulting viscous liquid to filtrate the unreacted reagent and byproduct. After the solution was dried over MgSO4 and evaporated, ethyl 2,2-bis(methylol)propionate (EtMPA) was obtained as a clear and colorless liquid (21.1 g, 86%). refluxed overnight The resins were then filtered out the filtrate was evaporated Methylene chloride (200 mL) was added to the resulting viscous liquid to filtrate the unreacted reagent and byproduct After the solution was dried over MgSO4 evaporated

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

実験手順: A solution of triphosgene (19.5 g, 0.065 mol) in CH2Cl2 (200 mL) was added stepwise to a CH2Cl2 solution (150 mL) of ethyl 2,2-bis(methylol)propionate (EtMPA) (21.1 g, 0.131 mol) and pyridine (64 mL, 0.786 mol) over 30 min at −75° C. with dry ice/acetone. The reaction mixture was kept stirring for another 2 hours under chilled condition and then allowed to heat to room temperature. Saturated NH4Cl aqueous solution (200 mL) was added to the reaction mixture to decompose excess triphosgene. The organic phase was then treated with 1 N HCl aq (200 mL), followed by saturated NaHCO3 (200 mL), brine (200 mL), and water (200 mL). After the CH2Cl2 solution was dried over MgSO4 and evaporated, the residue was recrystallized from ethyl acetate to give white crystals (13.8 g, 56%). 1H NMR: delta 4.68 (d, 2H, CH2OCOO), 4.25 (q, 1H, OCH2CH3), 4.19 (d, 2H, CH2OCOO), 1.32 (s, 3H, CH3), 1.29 (t, 3H, CH3CH2O). 13C NMR: delta 171.0, 147.5, 72.9, 62.1, 39.9, 17.3, 13.8. HR-ESI-MS: m/z calcd for C8H12O5; Na, 211.0582; found, 221.0578. under chilled condition After the CH2Cl2 solution was dried over MgSO4 evaporated the residue was recrystallized from ethyl acetate

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

実験手順: 2,2-Bis(methylol)propionic acid (bisMPA; molecular weight 134.1, 22.1 g, 0.165 mol) was added in ethanol (150 mL) with Amberlyst-15 (6.8 g) and refluxed overnight. The resins were then filtered out and the filtrate was evaporated. Methylene chloride (200 mL) was added to the resulting viscous liquid to filtrate the unreacted reagent and byproduct. After the solution was dried over MgSO4 and evaporated, ethyl 2,2-bis(methylol)propionate (EtMPA) was obtained as a clear and colorless liquid (21.1 g, 86%). refluxed overnight The resins were then filtered out the filtrate was evaporated Methylene chloride (200 mL) was added to the resulting viscous liquid to filtrate the unreacted reagent and byproduct After the solution was dried over MgSO4 evaporated