ethyl 5-(hydroxymethyl)furan-2-carboxylate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 0° C. solution of 5-hydroxymethyl-2-carboethoxyfuran (2.94 g, 17.3 mmol), prepared as in step 1, in CH2Cl2 (50 mL) was added 2,6-lutidine (2.50 mL, 21.5 mmol) and methanesulfonyl chloride (1.50 mL, 19.0 mmol). The reaction mixture was stirred for 40 min at 0° C., then the cold bath was removed and stirring was continued for 2 hours. The reaction mixture was extracted with 1N aqueous HCl and saturated aqueous NaHCO3, and the organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 5-methanesulfonyloxymethyl-2-carboethoxyfuran (4.0 g) as a yellow oil which was used without further purification. the cold bath was removed stirring was continued for 2 hours The reaction mixture was extracted with 1N aqueous HCl and saturated aqueous NaHCO3 the organic phase was dried over MgSO4 filtered concentrated in vacuo

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

Procedure: A solution of 5-acetoxymethyl-2-ethoxycarbonylfuran (Maybridge Chemical Co., Ltd., Tintagel, Cornwall, UK., 0.54 g, 2.5 mmol) and K2CO3 (0.352 g, 2.6 mmol) in 5:1THF/H2O (30 mL), was stirred for 17 hours at ambient temperature. The reaction mixture was concentrated in vacuo and the residue partitioned between CH2Cl2 and saturated aqueous NaHCO3. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 5-hydroxymethyl-2-carboethoxyfuran (0.32 g) as a yellow liquid which was used without further purification. The reaction mixture was concentrated in vacuo the residue partitioned between CH2Cl2 and saturated aqueous NaHCO3 The organic phase was dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 0° C. solution of 5-hydroxymethyl-2-carboethoxyfuran (2.94 g, 17.3 mmol), prepared as in step 1, in CH2Cl2 (50 mL) was added 2,6-lutidine (2.50 mL, 21.5 mmol) and methanesulfonyl chloride (1.50 mL, 19.0 mmol). The reaction mixture was stirred for 40 min at 0° C., then the cold bath was removed and stirring was continued for 2 hours. The reaction mixture was extracted with 1N aqueous HCl and saturated aqueous NaHCO3, and the organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 5-methanesulfonyloxymethyl-2-carboethoxyfuran (4.0 g) as a yellow oil which was used without further purification. the cold bath was removed stirring was continued for 2 hours The reaction mixture was extracted with 1N aqueous HCl and saturated aqueous NaHCO3 the organic phase was dried over MgSO4 filtered concentrated in vacuo

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

Procedure: A solution of 5-acetoxymethyl-2-ethoxycarbonylfuran (Maybridge Chemical Co., Ltd., Tintagel, Cornwall, UK., 0.54 g, 2.5 mmol) and K2CO3 (0.352 g, 2.6 mmol) in 5:1THF/H2O (30 mL), was stirred for 17 hours at ambient temperature. The reaction mixture was concentrated in vacuo and the residue partitioned between CH2Cl2 and saturated aqueous NaHCO3. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 5-hydroxymethyl-2-carboethoxyfuran (0.32 g) as a yellow liquid which was used without further purification. The reaction mixture was concentrated in vacuo the residue partitioned between CH2Cl2 and saturated aqueous NaHCO3 The organic phase was dried over MgSO4 filtered concentrated in vacuo

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

Procedure: A solution of 5-acetoxymethyl-2-ethoxycarbonylfuran (Maybridge Chemical Co., Ltd., Tintagel, Cornwall, UK., 0.54 g, 2.5 mmol) and K2CO3 (0.352 g, 2.6 mmol) in 5:1THF/H2O (30 mL), was stirred for 17 hours at ambient temperature. The reaction mixture was concentrated in vacuo and the residue partitioned between CH2Cl2 and saturated aqueous NaHCO3. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 5-hydroxymethyl-2-carboethoxyfuran (0.32 g) as a yellow liquid which was used without further purification. The reaction mixture was concentrated in vacuo the residue partitioned between CH2Cl2 and saturated aqueous NaHCO3 The organic phase was dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 0° C. solution of 5-hydroxymethyl-2-carboethoxyfuran (2.94 g, 17.3 mmol), prepared as in step 1, in CH2Cl2 (50 mL) was added 2,6-lutidine (2.50 mL, 21.5 mmol) and methanesulfonyl chloride (1.50 mL, 19.0 mmol). The reaction mixture was stirred for 40 min at 0° C., then the cold bath was removed and stirring was continued for 2 hours. The reaction mixture was extracted with 1N aqueous HCl and saturated aqueous NaHCO3, and the organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 5-methanesulfonyloxymethyl-2-carboethoxyfuran (4.0 g) as a yellow oil which was used without further purification. the cold bath was removed stirring was continued for 2 hours The reaction mixture was extracted with 1N aqueous HCl and saturated aqueous NaHCO3 the organic phase was dried over MgSO4 filtered concentrated in vacuo

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

Procedure: A solution of 5-acetoxymethyl-2-ethoxycarbonylfuran (Maybridge Chemical Co., Ltd., Tintagel, Cornwall, UK., 0.54 g, 2.5 mmol) and K2CO3 (0.352 g, 2.6 mmol) in 5:1THF/H2O (30 mL), was stirred for 17 hours at ambient temperature. The reaction mixture was concentrated in vacuo and the residue partitioned between CH2Cl2 and saturated aqueous NaHCO3. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 5-hydroxymethyl-2-carboethoxyfuran (0.32 g) as a yellow liquid which was used without further purification. The reaction mixture was concentrated in vacuo the residue partitioned between CH2Cl2 and saturated aqueous NaHCO3 The organic phase was dried over MgSO4 filtered concentrated in vacuo