No renderable structure data available
CC1(C(=CC(=O)O1)O)CChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-hydroxy-5,5-dimethylfuran-2-one |
|---|---|
| IUPAC Name | — |
| CAS Number | 22621-30-3 |
| Database ID | 54720139 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-hydroxy-5,5-dimethylfuran-2-one (CAS 22621-30-3) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 54720139
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3d434f141164459fb8cf3b250cc796f3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-hydroxy-5, 5-dimethyl-5H-furan-2-one (2.1 g, 16.4 mmol) in DCE (40 mL) and DMF (1.5 mL) at 0° C. was added dropwise oxalyl bromide (3.0 mL, 32 mmol, 2 equiv). The mixture was stirred at room temperature for 4-5 h, and then put in an ice bath. Ice water (100 mL) was added slowly. The mixture was extracted with CH2Cl2 (100 mL). The organic phase was washed with 10% NaHCO3 and again with water, dried over sodium sulfate and evaporated to give the title compound 2.7 g (86% yield). put in an ice bath The mixture was extracted with CH2Cl2 (100 mL) The organic phase was washed with 10% NaHCO3 and again with water dried over sodium sulfate evaporated
Source ID: ord-260a2582978345039ad1ee6764745a2eConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a −78° C. stirred solution of 4-hydroxy-5,5-dimethyl-5H-furan-2-one (250 mg, 1.95 mmol) in 18 mL of anhydrous CH2Cl2, was added triethylamine (0.40 mL, 2.9 mmol) and Tf2O (0.49 mL, 2.9 mmol). The reaction was stirred at −78° C. for 30 minutes, and quenched with saturated NH4Cl solution (10 mL). The mixture was warmed up to room temperature and separated. The aqueous layer was extracted with CH2Cl2 (2×20 mL). All organic layers were combined, dried over Na2SO4 and evaporated to brown oil, which was purified by plugging through a short pad of silica gel column with EtOAc/hexanes (1/3). Evaporation of solvents gave 2,2-dimethyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate as a light brown oil (450 mg, 89%). quenched with saturated NH4Cl solution (10 mL) The mixture was warmed up to room temperature separated The aqueous layer was extracted with CH2Cl2 (2×20 mL) dried over Na2SO4 evaporated to brown oil, which was purified Evaporation of solvents
Source ID: ord-5991e68c395a48ea8b9586856d436e16Conditions: temp:88.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of 5,5-dimethyl-4-pyrrolidin-1-ylfuran-2(5H)-one (535 mg) in a mixture of MeOH (2 mL) and 5M HCl (8 mL) was heated at 88° C. for 2 hours. The mixture was cooled to room temp., extracted with CHCl3 (10×15 mL), combined, dried over Na2SO4, and evaporated to dryness to give 4-hydroxy-5,5-dimethyl-5H-furan-2-one as light brown solid. Yield: 359 mg, 95%. The mixture was cooled to room temp. extracted with CHCl3 (10×15 mL) dried over Na2SO4 evaporated to dryness
Source ID: ord-78b0883288cf4de68deadf6efa90fd01Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-hydroxy-5,5-dimethyl-5H-furan-2-one (2.1 g, 16.4 mmol) in DCE (40 mL) and DMF (1.5 mL) at 0° C. was added dropwise oxalyl bromide (3.0 mL, 32 mmol, 2 equiv). The mixture was stirred at room temperature for 4-5 h, and then put in an ice bath. Ice water (100 mL) was added slowly. The mixture was extracted with CH2Cl2 (100 mL). The organic phase was washed with 10% NaHCO3 and again with water, dried over sodium sulfate and evaporated to give the title compound 2.7 g (86% yield). put in an ice bath The mixture was extracted with CH2Cl2 (100 mL) The organic phase was washed with 10% NaHCO3 and again with water dried over sodium sulfate evaporated
Source ID: ord-81dcf85130a4439ebe11d250cf52341fConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a −78° C. stirred solution of 4-hydroxy-5,5-dimethyl-5H-furan-2-one (250 mg, 1.95 mmol) in 18 mL of anhydrous CH2Cl2, was added triethylamine (0.40 mL, 2.9 mmol) and Tf2O (0.49 mL, 2.9 mmol). The reaction was stirred at −78° C. for 30 minutes, and quenched with saturated NH4Cl solution (10 mL). The mixture was warmed up to room temperature and separated. The aqueous layer was extracted with CH2Cl2 (2×20 mL). All organic layers were combined, dried over Na2SO4 and evaporated to brown oil, which was purified by plugging through a short pad of silica gel column with EtOAc/hexanes (1/3). Evaporation of solvents gave 2,2-dimethyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate as a light brown oil (450 mg, 89%). quenched with saturated NH4Cl solution (10 mL) The mixture was warmed up to room temperature separated The aqueous layer was extracted with CH2Cl2 (2×20 mL) dried over Na2SO4 evaporated to brown oil, which was purified Evaporation of solvents
Source ID: ord-31415ca79c424317887fa00da44f25a0Conditions: temp:88.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of 5,5-dimethyl-4-pyrrolidin-1-ylfuran-2(5H)-one (535 mg) in a mixture of MeOH (2 mL) and 5M HCl (8 mL) was heated at 88° C. for 2 hours. The mixture was cooled to room temp., extracted with CHCl3 (10×15 mL), combined, dried over Na2SO4, and evaporated to dryness to give 4-hydroxy-5,5-dimethyl-5H-furan-2-one as light brown solid. Yield: 359 mg, 95%. The mixture was cooled to room temp. extracted with CHCl3 (10×15 mL) dried over Na2SO4 evaporated to dryness
Source ID: ord-6057f08f280d40e299280dbdc5fb3106Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-hydroxy-5,5-dimethyl-5H-furan-2-one (2.1 g, 16.4 mmol) in DCE (40 mL) and DMF (1.5 mL) at 0° C. was added dropwise oxalyl bromide (3.0 mL, 32 mmol, 2 equiv). The mixture was stirred at room temperature for 4-5 h, and then put in an ice bath. Ice water (100 mL) was added slowly. The mixture was extracted with CH2Cl2 (100 mL). The organic phase was washed with 10% NaHCO3 and again with water, dried over sodium sulfate and evaporated to give the title compound 2.7 g (86% yield). put in an ice bath The mixture was extracted with CH2Cl2 (100 mL) The organic phase was washed with 10% NaHCO3 and again with water dried over sodium sulfate evaporated
Source ID: ord-6da8bd8f3fc74f12a5427d1604e9f269Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-hydroxy-5,5-dimethyl-5H-furan-2-one (2.1 g, 16.4 mmol) in DCE (40 mL) and DMF (1.5 mL) at 0° C. was added dropwise oxalyl bromide (3.0 mL, 32 mmol, 2 equiv). The mixture was stirred at room temperature for 4-5 h, and then put in an ice bath. Ice water (100 mL) was added slowly. The mixture was extracted with CH2Cl2 (100 mL). The organic phase was washed with 10% NaHCO3 and again with water, dried over sodium sulfate and evaporated to give the title compound 2.7 g (86% yield). put in an ice bath The mixture was extracted with CH2Cl2 (100 mL) The organic phase was washed with 10% NaHCO3 and again with water dried over sodium sulfate evaporated
Source ID: ord-6da8bd8f3fc74f12a5427d1604e9f269Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a −78° C. stirred solution of 4-hydroxy-5,5-dimethyl-5H-furan-2-one (250 mg, 1.95 mmol) in 18 mL of anhydrous CH2Cl2, was added triethylamine (0.40 mL, 2.9 mmol) and Tf2O (0.49 mL, 2.9 mmol). The reaction was stirred at −78° C. for 30 minutes, and quenched with saturated NH4Cl solution (10 mL). The mixture was warmed up to room temperature and separated. The aqueous layer was extracted with CH2Cl2 (2×20 mL). All organic layers were combined, dried over Na2SO4 and evaporated to brown oil, which was purified by plugging through a short pad of silica gel column with EtOAc/hexanes (1/3). Evaporation of solvents gave 2,2-dimethyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate as a light brown oil (450 mg, 89%). quenched with saturated NH4Cl solution (10 mL) The mixture was warmed up to room temperature separated The aqueous layer was extracted with CH2Cl2 (2×20 mL) dried over Na2SO4 evaporated to brown oil, which was purified Evaporation of solvents
Source ID: ord-dbf4dfca10f742b8b68d1a2721a6fb16Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a −78° C. stirred solution of 4-hydroxy-5,5-dimethyl-5H-furan-2-one (250 mg, 1.95 mmol) in 18 mL of anhydrous CH2Cl2, was added triethylamine (0.40 mL, 2.9 mmol) and Tf2O (0.49 mL, 2.9 mmol). The reaction was stirred at −78° C. for 30 minutes, and quenched with saturated NH4Cl solution (10 mL). The mixture was warmed up to room temperature and separated. The aqueous layer was extracted with CH2Cl2 (2×20 mL). All organic layers were combined, dried over Na2SO4 and evaporated to brown oil, which was purified by plugging through a short pad of silica gel column with EtOAc/hexanes (1/3). Evaporation of solvents gave 2,2-dimethyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate as a light brown oil (450 mg, 89%). quenched with saturated NH4Cl solution (10 mL) The mixture was warmed up to room temperature separated The aqueous layer was extracted with CH2Cl2 (2×20 mL) dried over Na2SO4 evaporated to brown oil, which was purified Evaporation of solvents
Source ID: ord-dbf4dfca10f742b8b68d1a2721a6fb16Conditions: temp:88.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of 5,5-dimethyl-4-pyrrolidin-1-ylfuran-2(5H)-one (535 mg) in a mixture of MeOH (2 mL) and 5M HCl (8 mL) was heated at 88° C. for 2 hours. The mixture was cooled to room temp., extracted with CHCl3 (10×15 mL), combined, dried over Na2SO4, and evaporated to dryness to give 4-hydroxy-5,5-dimethyl-5H-furan-2-one as light brown solid. Yield: 359 mg, 95%. The mixture was cooled to room temp. extracted with CHCl3 (10×15 mL) dried over Na2SO4 evaporated to dryness
Source ID: ord-5f75305b2f2e40abb74ffdea41f99db7PubChem References
These sources are listed in the compound's public database record.
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