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CC1(OCC(O1)C=O)CChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2,2-dimethyl-1,3-dioxolane-4-carbaldehyde |
|---|---|
| IUPAC Name | — |
| CAS Number | 5736-03-8 |
| Database ID | 110702 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (CAS 5736-03-8) 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 110702
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-3f12d53ed75645278d4b4921080161b1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 3-(1-methylindol-3-yl)-4-(3-aminophenyl)-1H-pyrrole-2,5-dione (100 mg, 0.32 mmol) and 2,2-dimethyldioxolane-4-carboxaldehyde (0.38 mmol) (prepared as described in Kumont, von R., et al. Helv. Chim. Acta., 66, 814, (1983)) in dichloromethane (12 mL) was stirred at room temperature for 10 min., and then Na(OAc)3BH (120 mg, 0.57 mmol) was added. The reaction mixture was stirred overnight and then partition between EtOAc and H20. The organic layer was separated, washed with water and concentrated. The crude product was purified by preparatory TLC with 3/1 hexanes/EtOAc to give 3-(1-methylindol-3-yl)-4-[3-(2,2-dimethyldioxolan-4-ylmethylamino)phenyl]-1H-pyrrole-2,5-dione (32.6 mg, 24%). The reaction mixture was stirred overnight partition between EtOAc and H20 The organic layer was separated washed with water concentrated The crude product was purified by preparatory TLC with 3/1 hexanes/EtOAc
Source ID: ord-bb4da6f1b1944bd3b2902e2850851aa2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of propylamine (0.72 mL, 7.7 mmol) and 2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (1.0 g, 7.7 mmol) in 1,2-dichloroethane (25 mL) was added sodium triacetoxyborohydride (2.28 g, 10.8 mmol). The mixture was stirred for 1.5 h at room temperature. The reaction mixture was then quenched with sat'd aq NaHCO3 and extracted with EtOAc. The organic layer was dried with MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (CH2Cl2 to 10% MeOH in CH2Cl2, gradient) to afford 1.26 g (73%) of N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)propan-1-amine. The reaction mixture was then quenched with sat'd aq NaHCO3 extracted with EtOAc The organic layer was dried with MgSO4 filtered concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (CH2Cl2 to 10% MeOH in CH2Cl2, gradient)
Source ID: ord-a8eb68fa38d04981945bcca9a25c70a9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of propylamine (0.72 mL, 7.7 mmol) and 2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (1.0 g, 7.7 mmol) in 1,2-dichloroethane (25 mL) was added sodium triacetoxyborohydride (2.28 g, 10.8 mmol). The mixture was stirred for 1.5 h at room temperature. The reaction mixture was then quenched with sat'd aq NaHCO3 and extracted with EtOAc. The organic layer was dried with MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (CH2Cl2 to 10% MeOH in CH2Cl2, gradient) to afford 1.26 g (73%) of N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)propan-1-amine. The reaction mixture was then quenched with sat'd aq NaHCO3 extracted with EtOAc The organic layer was dried with MgSO4 filtered concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (CH2Cl2 to 10% MeOH in CH2Cl2, gradient)
Source ID: ord-a8eb68fa38d04981945bcca9a25c70a9Conditions: temp:-60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of anhydrous DMSO (3.41 mL, 48 mmol) in CH2Cl2 (5 mL) was added dropwise to a stirred solution of oxalyl chloride (1.92 mL, 22 mmol) in CH2Cl2 (50 mL) at −60° C. To this mixture was added a solution of (2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (2.48 mL, 20 mmol) in CH2Cl2 (10 mL). The resulting mixture was stirred for 15 min at −60° C. TEA (13.9 mL, 100 mmol) was added dropwise. The reaction mixture was then warmed to room temperature. Water (50 mL) and CH2Cl2 (50 mL) were added. The organic layer was separated and washed with water (25 mL). The aqueous layer was extracted with CH2Cl2 (3×50 mL). The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to afford the crude 2,2-dimethyl-1,3-dioxolane-4-carbaldehyde that was used directly without further purification. The reaction mixture was then warmed to room temperature The organic layer was separated washed with water (25 mL) The aqueous layer was extracted with CH2Cl2 (3×50 mL) The organic layers were dried over MgSO4 filtered concentrated under reduced pressure
Source ID: ord-cb8ab75ac5b34eb38eb55a4c4112ef1cConditions: temp:-60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of anhydrous DMSO (3.41 mL, 48 mmol) in CH2Cl2 (5 mL) was added dropwise to a stirred solution of oxalyl chloride (1.92 mL, 22 mmol) in CH2Cl2 (50 mL) at −60° C. To this mixture was added a solution of (2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (2.48 mL, 20 mmol) in CH2Cl2 (10 mL). The resulting mixture was stirred for 15 min at −60° C. TEA (13.9 mL, 100 mmol) was added dropwise. The reaction mixture was then warmed to room temperature. Water (50 mL) and CH2Cl2 (50 mL) were added. The organic layer was separated and washed with water (25 mL). The aqueous layer was extracted with CH2Cl2 (3×50 mL). The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to afford the crude 2,2-dimethyl-1,3-dioxolane-4-carbaldehyde that was used directly without further purification. The reaction mixture was then warmed to room temperature The organic layer was separated washed with water (25 mL) The aqueous layer was extracted with CH2Cl2 (3×50 mL) The organic layers were dried over MgSO4 filtered concentrated under reduced pressure
Source ID: ord-cb8ab75ac5b34eb38eb55a4c4112ef1cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of propylamine (0.72 mL, 7.7 mmol) and 2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (1.0 g, 7.7 mmol) in 1,2-dichloroethane (25 mL) was added sodium triacetoxyborohydride (2.28 g, 10.8 mmol). The mixture was stirred for 1.5 h at room temperature. The reaction mixture was then quenched with sat'd aq NaHCO3 and extracted with EtOAc. The organic layer was dried with MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (CH2Cl2 to 10% MeOH in CH2Cl2, gradient) to afford 1.26 g (73%) of N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)propan-1-amine. The reaction mixture was then quenched with sat'd aq NaHCO3 extracted with EtOAc The organic layer was dried with MgSO4 filtered concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (CH2Cl2 to 10% MeOH in CH2Cl2, gradient)
Source ID: ord-3cf4e12ef20e427cba563ac0e925fe95Conditions: temp:-60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of anhydrous DMSO (3.41 mL, 48 mmol) in CH2Cl2 (5 mL) was added dropwise to a stirred solution of oxalyl chloride (1.92 mL, 22 mmol) in CH2Cl2 (50 mL) at −60° C. To this mixture was added a solution of (2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (2.48 mL, 20 mmol) in CH2Cl2 (10 mL). The resulting mixture was stirred for 15 min at −60° C. TEA (13.9 mL, 100 mmol) was added dropwise. The reaction mixture was then warmed to room temperature. Water (50 mL) and CH2Cl2 (50 mL) were added. The organic layer was separated and washed with water (25 mL). The aqueous layer was extracted with CH2Cl2 (3×50 mL). The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to afford the crude 2,2-dimethyl-1,3-dioxolane-4-carbaldehyde that was used directly without further purification. The reaction mixture was then warmed to room temperature The organic layer was separated washed with water (25 mL) The aqueous layer was extracted with CH2Cl2 (3×50 mL) The organic layers were dried over MgSO4 filtered concentrated under reduced pressure
Source ID: ord-0ecb885addee473b936a27c496770b68Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of propylamine (0.72 mL, 7.7 mmol) and 2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (1.0 g, 7.7 mmol) in 1,2-dichloroethane (25 mL) was added sodium triacetoxyborohydride (2.28 g, 10.8 mmol). The mixture was stirred for 1.5 h at room temperature. The reaction mixture was then quenched with sat'd aq NaHCO3 and extracted with EtOAc. The organic layer was dried with MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (CH2Cl2 to 10% MeOH in CH2Cl2, gradient) to afford 1.26 g (73%) of N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)propan-1-amine. The reaction mixture was then quenched with sat'd aq NaHCO3 extracted with EtOAc The organic layer was dried with MgSO4 filtered concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (CH2Cl2 to 10% MeOH in CH2Cl2, gradient)
Source ID: ord-3cf4e12ef20e427cba563ac0e925fe95Conditions: temp:-60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of anhydrous DMSO (3.41 mL, 48 mmol) in CH2Cl2 (5 mL) was added dropwise to a stirred solution of oxalyl chloride (1.92 mL, 22 mmol) in CH2Cl2 (50 mL) at −60° C. To this mixture was added a solution of (2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (2.48 mL, 20 mmol) in CH2Cl2 (10 mL). The resulting mixture was stirred for 15 min at −60° C. TEA (13.9 mL, 100 mmol) was added dropwise. The reaction mixture was then warmed to room temperature. Water (50 mL) and CH2Cl2 (50 mL) were added. The organic layer was separated and washed with water (25 mL). The aqueous layer was extracted with CH2Cl2 (3×50 mL). The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to afford the crude 2,2-dimethyl-1,3-dioxolane-4-carbaldehyde that was used directly without further purification. The reaction mixture was then warmed to room temperature The organic layer was separated washed with water (25 mL) The aqueous layer was extracted with CH2Cl2 (3×50 mL) The organic layers were dried over MgSO4 filtered concentrated under reduced pressure
Source ID: ord-0ecb885addee473b936a27c496770b68PubChem References
These sources are listed in the compound's public database record.
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