(5-methylfuran-2-yl)methanol

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N-Dimethylformamide dineopentyl acetal (1.8 ml) was added to a stirred suspension of 5-chloropyrimidin-2-one (522 mg) and 2-hydroxymethyl-5-methylfuran (628 mg) in dry N,N-dimethylformamide (10 ml) under nitrogen. The resulting solution was then stirred and heated at 90° C. under nitrogen. After 1.5 h the reaction mixture was evaporated to a brown crystalline solid (1.030 g). The solid was subjected to column chromatography on silica (70-230 mesh) (100 g) developing with chloroform-ethanol, 29:1. The resulting pale yellow solid (327 mg) was crystallised twice from acetone to give white needles of the title furan (206 mg), m.p. 166°-167° C., λmax 226 nm (ε 15,660), 332 nm (ε 2,520), λinf 247 nm (ε 3,100). After 1.5 h the reaction mixture was evaporated to a brown crystalline solid (1.030 g) The resulting pale yellow solid (327 mg) was crystallised twice from acetone

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N-Dimethylformamide dineopentyl acetal (1.8 ml) was added to a stirred suspension of 5-chloropyrimidin-2-one (522 mg) and 2-hydroxymethyl-5-methylfuran (628 mg) in dry N,N-dimethylformamide (10 ml) under nitrogen. The resulting solution was then stirred and heated at 90° C. under nitrogen. After 1.5 h the reaction mixture was evaporated to a brown crystalline solid (1.030 g). The solid was subjected to column chromatography on silica (70-230 mesh) (100 g) developing with chloroform-ethanol, 29:1. The resulting pale yellow solid (327 mg) was crystallised twice from acetone to give white needles of the title furan (206 mg), m.p. 166°-167° C., λmax 226 nm (ε 15,660), 332 nm (ε 2,520), λinf 247 nm (ε 3,100). After 1.5 h the reaction mixture was evaporated to a brown crystalline solid (1.030 g) The resulting pale yellow solid (327 mg) was crystallised twice from acetone

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

Procedure: Diethylazodicarboxylate (1.13 mL 5.83 mmol) was added dropwise to a solution of (E)-3-(3-acetoxy-4-methoxy-phenyl)-N-(3-hydroxy-phenyl)-acrylamide (0.763 g, 2.33 mmol), (5-methyl-furan-2-yl)-methanol (0.392 g, 3.5 mmol) and triphenylphosphine (1.53 g, 5.83 mmol) in dry THF (20 mL) at 0° C. The resulting solution was allowed to reach RT and stirred for 16 hrs. The reaction mixture was then diluted with DCM and washed with water, aqueous hydrochloric acid, and brine. The organic layer was then dried over sodium sulphate and evaporated. The resulting raw material was taken up, without further purification, with a 3N methanolic solution of hydrochloric acid (5 mL-15 mmols) and stirred at RT for 16 hrs, concentrated under reduced pressure, taken up with solvent an re-evaporated (3 times with MeOH and once with acetone) to give a residue that was purified by silica gel column chromatography (eluant DCM/MeOH 98/2) to obtain 15 mg of the title (E)-3-(3-hydroxy-4-methoxy-phenyl)-N-[3-(5-methyl-furan-2-ylmethoxy)-phenyl]-acrylamide. to reach RT washed with water, aqueous hydrochloric acid, and brine The organic layer was then dried over sodium sulphate evaporated The resulting raw material was taken up, without further purification, with a 3N methanolic solution of hydrochloric acid (5 mL-15 mmols) stirred at RT for 16 hrs concentrated under reduced pressure an re-evaporated (3 times with MeOH once with acetone) to give a residue that was purified by silica gel column chromatography (eluant DCM/MeOH 98/2)

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

Procedure: Diethylazodicarboxylate (1.13 mL 5.83 mmol) was added dropwise to a solution of (E)-3-(3-acetoxy-4-methoxy-phenyl)-N-(3-hydroxy-phenyl)-acrylamide (0.763 g, 2.33 mmol), (5-methyl-furan-2-yl)-methanol (0.392 g, 3.5 mmol) and triphenylphosphine (1.53 g, 5.83 mmol) in dry THF (20 mL) at 0° C. The resulting solution was allowed to reach RT and stirred for 16 hrs. The reaction mixture was then diluted with DCM and washed with water, aqueous hydrochloric acid, and brine. The organic layer was then dried over sodium sulphate and evapored. The resulting raw material was taken up, without further purification, with a 3N methanolic solution of hydrochloric acid (5 mL-15 mmols) and stirred at RT for 16 hrs, concentrated under reduced pressure, taken up with solvent an re-evaporated (3 times with MeOH and once with acetone) to give a residue that was purified by silica gel column chromatography (eluant DCM/MeOH 98/2) to obtain 15 mg of the title (E)-3-(3-hydroxy-4-methoxy-phenyl)-N-[3-(5-methyl-furan-2-ylmethoxy)-phenyl]-acrylamide. to reach RT washed with water, aqueous hydrochloric acid, and brine The organic layer was then dried over sodium sulphate The resulting raw material was taken up, without further purification, with a 3N methanolic solution of hydrochloric acid (5 mL-15 mmols) stirred at RT for 16 hrs concentrated under reduced pressure an re-evaporated (3 times with MeOH once with acetone) to give a residue that was purified by silica gel column chromatography (eluant DCM/MeOH 98/2)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N-Dimethylformamide dineopentyl acetal (1.8 ml) was added to a stirred suspension of 5-chloropyrimidin-2-one (522 mg) and 2-hydroxymethyl-5-methylfuran (628 mg) in dry N,N-dimethylformamide (10 ml) under nitrogen. The resulting solution was then stirred and heated at 90° C. under nitrogen. After 1.5 h the reaction mixture was evaporated to a brown crystalline solid (1.030 g). The solid was subjected to column chromatography on silica (70-230 mesh) (100 g) developing with chloroform-ethanol, 29:1. The resulting pale yellow solid (327 mg) was crystallised twice from acetone to give white needles of the title furan (206 mg), m.p. 166°-167° C., λmax 226 nm (ε 15,660), 332 nm (ε 2,520), λinf 247 nm (ε 3,100). After 1.5 h the reaction mixture was evaporated to a brown crystalline solid (1.030 g) The resulting pale yellow solid (327 mg) was crystallised twice from acetone