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1-[5-(hydroxymethyl)furan-2-yl]ethanone (CAS 55087-82-6) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
想定用途
専門的研究・工業用途限定
データベース ID 580381
安全上の注意
For professional research and industrial use only. Review the supplier safety data sheet before handling.
合成データ
10 反応 · 10 文献
反応条件: temp:0.00; pressure:0.00; stir:
ソース ID: ord-1e2c3affd7664ea88a00737457c14a7a反応条件: temp:0.00; pressure:0.00; stir:
ソース ID: ord-083ba9a837e14f37a4f840c99978f69d反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(5-hydroxymethyl-furan-2-yl)-ethanone (2.00 g, 14.27 mmol) in dry CH2Cl2 (29 mL) was treated at 0° C. with Et3N (2.58 mL, 18.55 mmol) followed by DMAP (178 mg, 1.43 mmol) and Ms-Cl (1.33 mL, 17.13 mmol). After stirring at rt for 3 h, the reaction was quenched with water. The layers were separated and the aq. layer extracted with CH2Cl2 (3×). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give crude 1-(5-chloromethyl-furan-2-yl)-ethanone as a brown oil. Part of this crude material (2.33 g, 14.72 mmol) was dissolved in dry DMF (50 mL) and treated with NaN3 (2.90 g, 44.16 mmol) at 80° C. for 24 h. The reaction mixture was then cooled down to rt and partitioned between EA and water. The layers were separated and the aq. layer extracted with EA (1×). The combined org. extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to give crude 1-(5-azidomethyl-furan-2-yl)-ethanone as a brown oil. LC-MS-conditions 02: tR=0.81 min; [M+AcCN+H]+=207.50. the reaction was quenched with water The layers were separated the aq. layer extracted with CH2Cl2 (3×) layer was dried over MgSO4 filtered the solvents were removed under reduced pressure
ソース ID: ord-4970143265d64496877e57da29f393a4反応条件: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: Crude 1-[5-(tetrahydro-pyran-2-yloxymethyl)-furan-2-yl]-ethanone (89 g, 0.40 mol) was dissolved in MeOH (500 mL) and treated with Amberlyst 15 (15 g) at rt. The reaction mixture was stirred at 35° C. for 1 h, cooled to rt and filtered over celite. Et3N (1 mL) was added and the mixture was evaporated to dryness. The residue was stripped with methylcyclohexane and 1-(5-hydroxymethyl-furan-2-yl)ethanone was obtained as a yellow oil that solidified on standing. cooled to rt filtered over celite Et3N (1 mL) was added the mixture was evaporated to dryness
ソース ID: ord-6f3499ce65ce4f8eaa4b2d55b7c0b329反応条件: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: Crude 1-[5-(tetrahydro-pyran-2-yloxymethyl)-furan-2-yl]-ethanone (89 g, 0.40 mol) was dissolved in MeOH (500 mL) and treated with Amberlyst 15 (15 g) at rt. The reaction mixture was stirred at 35° C. for 1 h, cooled to rt and filtered over celite. Et3N (1 mL) was added and the mixture was evaporated to dryness. The residue was stripped with methylcyclohexane and 1-(5-hydroxymethyl-furan-2-yl)ethanone was obtained as a yellow oil that solidified on standing. cooled to rt filtered over celite Et3N (1 mL) was added the mixture was evaporated to dryness
ソース ID: ord-6f3499ce65ce4f8eaa4b2d55b7c0b329反応条件: temp:0.00; pressure:0.00; stir:
ソース ID: ord-083ba9a837e14f37a4f840c99978f69d反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(5-hydroxymethyl-furan-2-yl)-ethanone (2.00 g, 14.27 mmol) in dry CH2Cl2 (29 mL) was treated at 0° C. with Et3N (2.58 mL, 18.55 mmol) followed by DMAP (178 mg, 1.43 mmol) and Ms-Cl (1.33 mL, 17.13 mmol). After stirring at rt for 3 h, the reaction was quenched with water. The layers were separated and the aq. layer extracted with CH2Cl2 (3×) The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give 3.93 g (quant.) of crude 1-(5-chloromethyl-furan-2-yl)-ethanone as a brown oil. Part of this crude material (1.718 g, 10.83 mmol) in DMF (10.3 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (10.30 g of a 10% solution in acetone, 9.03 mmol) in DMF (10.3 mL) pre-treated for 30 min with DIPEA (3.09 mL, 18.06 mmol) and the reaction mixture was stirred overnight at 50° C. Water (32 mL), followed by EA (65 mL) were added. The aq. layer was extracted with EA (65 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (2:1 hept-EA) gave the title compound as a yellow solid: TLC:rf (2:1 hept-EA)=0.20. LC-MS-conditions 02: tR=0.85 min, [M+H]+=237.46. the reaction was quenched with water The layers were separated the aq. layer extracted with CH2Cl2 (3×) The org layer was dried over MgSO4 filtered the solvents were removed under reduced pressure
ソース ID: ord-61492e4edbd74c4ab292dbec0f64616c反応条件: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: Crude 1-[5-(tetrahydro-pyran-2-yloxymethyl)-furan-2-yl]-ethanone (89 g, 0.40 mol) was dissolved in MeOH (500 mL) and treated with Amberlyst 15 (15 g) at rt. The reaction mixture was stirred at 35° C. for 1 h, cooled to rt and filtered over celite. Et3N (1 mL) was added and the mixture was evaporated to dryness. The residue was stripped with methylcyclohexane and 1-(5-hydroxymethyl-furan-2-yl)-ethanone (55 g, 99%) was obtained as a yellow oil that solidified on standing. cooled to rt filtered over celite Et3N (1 mL) was added the mixture was evaporated to dryness
ソース ID: ord-9e1f1aa9853443f58b1b2fead314e3fc反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(5-hydroxymethyl-furan-2-yl)-ethanone (2.00 g, 14.27 mmol) in dry CH2Cl2 (29 mL) was treated at 0° C. with Et3N (2.58 mL, 18.55 mmol) followed by DMAP (178 mg, 1.43 mmol) and Ms-Cl (1.33 mL, 17.13 mmol). After stirring at rt for 3 h, the reaction was quenched with water. The layers were separated and the aq. layer extracted with CH2Cl2 (3×). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give crude 1-(5-chloromethyl-furan-2-yl)-ethanone as a brown oil. Part of this crude material (2.33 g, 14.72 mmol) was dissolved in dry DMF (50 mL) and treated with NaN3 (2.90 g, 44.16 mmol) at 80° C. for 24 h. The reaction mixture was then cooled down to rt and partitioned between EA and water. The layers were separated and the aq. layer extracted with EA (1×). The combined org. extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to give crude 1-(5-azidomethyl-furan-2-yl)-ethanone as a brown oil. LC-MS-conditions 02: tR=0.81 min; [M+AcCN+H]+=207.50. the reaction was quenched with water The layers were separated the aq. layer extracted with CH2Cl2 (3×) layer was dried over MgSO4 filtered the solvents were removed under reduced pressure
ソース ID: ord-4970143265d64496877e57da29f393a4反応条件: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: Crude 1-[5-(tetrahydro-pyran-2-yloxymethyl)-furan-2-yl]-ethanone (89 g, 0.40 mol) was dissolved in MeOH (500 mL) and treated with Amberlyst 15 (15 g) at rt. The reaction mixture was stirred at 35° C. for 1 h, cooled to rt and filtered over celite. Et3N (1 mL) was added and the mixture was evaporated to dryness. The residue was stripped with methylcyclohexane and 1-(5-hydroxymethyl-furan-2-yl)ethanone was obtained as a yellow oil that solidified on standing. cooled to rt filtered over celite Et3N (1 mL) was added the mixture was evaporated to dryness
ソース ID: ord-6f3499ce65ce4f8eaa4b2d55b7c0b329PubChem References
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