Product Details of [ 113602-62-3 ]
CAS No. : | 113602-62-3 | MDL No. : | MFCD12924083 |
Formula : | C7H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HJHSYAMEFMNNBD-UHFFFAOYSA-N |
M.W : | 155.15 | Pubchem ID : | 54697147 |
Synonyms : |
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Computed Properties of [ 113602-62-3 ]
TPSA :Topological Polar Surface Area |
51.5 |
H-Bond Acceptor Count : |
3 |
XLogP3 : |
1 |
H-Bond Donor Count : |
1 |
SP3 : |
0.29 |
Rotatable Bond Count : |
2 |
Safety of [ 113602-62-3 ]
Application In Synthesis of [ 113602-62-3 ]
- Upstream synthesis route of [ 113602-62-3 ]
- Downstream synthetic route of [ 113602-62-3 ]
- 1
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[ 74-89-5 ]

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[ 147624-81-5 ]

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[ 113602-62-3 ]
- 2
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[ 113602-62-3 ]

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[ 150713-75-0 ]
Yield | Reaction Conditions | Operation in experiment |
42% |
With N-Bromosuccinimide; In tetrahydrofuran; methanol; at 0 - 20℃; for 4.0h; |
General procedure: NBS (63 mg,0.35 mmol) was added to a solution of 1 (100 mg, 0.70 mmol) in 10 mL of THF - CH3OH (1:1, v/v) at 0 C and the mixture was stirred at roomtemperature. After 2 h, NBS (50.4 mg, 0.28 mmol) was added again to the mixture at 0 C, and it was stirred at room temperature for 2 h. The solvent wasremoved in vacuo, and water (15 mL) was added to the residue. The aqueouslayer was extracted three times with EtOAc (30 mL). The organic layers weregathered together, washed with water and brine, dried over MgSO4, filtered,and concentrated in vacuo. Et2O (10 mL) was added to the dry residue todiscard succinimide. The filtrate was concentrated in vacuo, and heptane(10 mL) was added to the dry residue to afford 4 as an orange powder (68.6 mg,44% yield). |
- 3
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[ 113602-62-3 ]

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methyl 5-chloro-3-hydroxy-1-methyl-1H-pyrrol-2-yl-carboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
7% |
With sulfuryl dichloride; In dichloromethane; at 20℃; for 12.0h; |
General procedure: SO2Cl2 (5 M in CH2Cl2, 1.42 mL, 7.09 mmol) was added to a solution of 2 (1 g, 6.44 mmol) in CH2Cl2 (5 mL), and the mixture was stirred during 1 hour at room temperature.The mixture was concentrated in vacuo and the dry residue was purifiedby column chromatography on silica gel (EtOAc - heptane, gradient 1:0 to 7:3,v/v) to afford 8 as a yellowish solid (640 mg, 52% yield). |
- 4
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[ 113602-62-3 ]

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methyl 4,5-dichloro-3-hydroxy-1-methyl-1H-pyrrol-2-yl-carboxylate
[ No CAS ]

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methyl 5-chloro-3-hydroxy-1-methyl-1H-pyrrol-2-yl-carboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
1%; 52% |
With sulfuryl dichloride; In dichloromethane; at 20℃; for 36.0h; |
General procedure: SO2Cl2 (5 M in CH2Cl2, 1.42 mL, 7.09 mmol) was added to a solution of 2 (1 g, 6.44 mmol) in CH2Cl2 (5 mL), and the mixture was stirred during 1 hour at room temperature.The mixture was concentrated in vacuo and the dry residue was purifiedby column chromatography on silica gel (EtOAc - heptane, gradient 1:0 to 7:3,v/v) to afford 8 as a yellowish solid (640 mg, 52% yield). |
- 5
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[ 113602-62-3 ]

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methyl 4,5-dichloro-3-hydroxy-1-methyl-1H-pyrrol-2-yl-carboxylate
[ No CAS ]

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dimethyl 3',4-dichloro-4'-hydroxy-1,1'-dimethyl-3-oxo-2,3-dihydro-1H,1'H-[2,2'-bispyrrole]-2,5'-dicarboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
11% |
With sulfuryl dichloride; zinc; In dichloromethane; at 20℃; for 24.0h; |
General procedure: SO2Cl2 (5 M in CH2Cl2, 1.42 mL, 7.09 mmol) was added to a solution of 2 (1 g, 6.44 mmol) in CH2Cl2 (5 mL), and the mixture was stirred during 1 hour at room temperature.The mixture was concentrated in vacuo and the dry residue was purifiedby column chromatography on silica gel (EtOAc - heptane, gradient 1:0 to 7:3,v/v) to afford 8 as a yellowish solid (640 mg, 52% yield). |
- 6
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[ 113602-62-3 ]

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methyl 4-chloro-3-hydroxy-1-methyl-1H-pyrrol-2-yl-carboxylate
[ No CAS ]

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methyl 4,5-dichloro-3-hydroxy-1-methyl-1H-pyrrol-2-yl-carboxylate
[ No CAS ]

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methyl 5-chloro-3-hydroxy-1-methyl-1H-pyrrol-2-yl-carboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
2%; 4%; 9% |
With sulfuryl dichloride; In dichloromethane; at 40℃; for 1.0h;Irradiation; |
General procedure: SO2Cl2 (5 M in CH2Cl2, 1.42 mL, 7.09 mmol) was added to a solution of 2 (1 g, 6.44 mmol) in CH2Cl2 (5 mL), and the mixture was stirred during 1 hour at room temperature.The mixture was concentrated in vacuo and the dry residue was purifiedby column chromatography on silica gel (EtOAc - heptane, gradient 1:0 to 7:3,v/v) to afford 8 as a yellowish solid (640 mg, 52% yield). |
- 7
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[ 113602-62-3 ]

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[ 113602-65-6 ]
Yield | Reaction Conditions | Operation in experiment |
|
With bromine; In water; acetic acid; |
EXAMPLE 105 Methyl 4,5-dibromo-3-hydroxy-1-methyl-1H-pyrrole-2-carboxylate Methyl 3-hydroxy-1-methyl-1H-pyrrole-2-carboxylate (5.0 g, 0.032 moles) is dissolved in acetic acid (50 mL) and stirred at room temperature while bromine (3.3 mL, 0.065 moles) is added dropwise. After 1 hour the mixture is stirred into water (250 mL) and the precipitate is collected by filtration, rinsed several times with water and dried to afford the pure product (6.9 g); mp 128-130 C. |
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With bromine; In water; acetic acid; |
EXAMPLE 105 Methyl 4,5-dibromo-3-hydroxy-1-methyl-1 H -pyrrole-2-carboxylate. Methyl 3-hydroxy-1-methyl-1 H -pyrrole-2-carboxylate (5.0 g, 0.032 moles) is dissolved in acetic acid (50 mL) and stirred at room temperature while bromine (3.3 mL, 0.065 moles) is added dropwise. After 1 hour the mixture is stirred into water (250 mL) and the precipitate is collected by filtration, rinsed several times with water and dried to afford the pure product (6.9 g); mp 128-130C. |
- 8
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[ 80-63-7 ]

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[ 5473-12-1 ]

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[ 113602-62-3 ]
Yield | Reaction Conditions | Operation in experiment |
|
With sodium; In methanol; water; pentane; |
EXAMPLE 101 Methyl 3-hydroxy-1-methyl-1H-pyrrole-2-carboxylate Methyl sarcosinate (14.5 g, 0.14 moles) is added dropwise to methyl alpha-chloroacrylate (16.9 g, 0.14 moles), stirred and cooled in an ice bath. After 15 minutes the mixture is dissolved in methanol (30 mL) and added dropwise to a solution of sodium (9.7 g, 0.42 moles) in methanol (125 mL) under argon. After 18 hours at room temperature, the mixture is stripped of methanol under reduced pressure. The residue is taken up in water (300 mL), acidified with H3 PO4, and extracted with ethyl acetate (5*100 mL). The combined extracts are dried over MgSO4, concentrated under reduced pressure and filtered through a short column of silica gel. The filtrate is stripped of solvent under reduced pressure, leaving the product (16.5 g) as an oil sufficiently pure for further use. An analytically pure sample was obtained by vacuum distillation; bp 61-64 C. (0.5 mm) followed by recrystallization of the distillate from n-pentane to afford the product as shiny white crystals; mp 44-46 C. |
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With sodium; In methanol; water; pentane; |
EXAMPLE 101 Methyl 3-hydroxy-1-methyl-1 H -pyrrole-2-carboxylate. Methyl sarcosinate (14.5 g, 0.14 moles) is added dropwise to methyl alpha-chloroacrylate (16.9 g, 0.14 moles), stirred and cooled in an ice bath. After 15 minutes the mixture is dissolved in methanol (30 mL) and added dropwise to a solution of sodium (9.7 g, 0.42 moles) in methanol (125 mL) under argon. After 18 hours at room temperature, the mixture is stripped of methanol under reduced pressure. The residue is taken up in water (300 mL), acidified with H3PO4, and extracted with ethyl acetate (5*100 mL). The combined extracts are dried over MgSO4, concentrated under reduced pressure and filtered through a short column of silica gel. The filtrate is stripped of solvent under reduced pressure, leaving the product (16.5 g) as an oil sufficiently pure for further use. An analytically pure sample was obtained by vacuum distillation; bp 61-64C (0.5 mm) followed by recrystallization of the distillate from n-pentane to afford the product as shiny white crystals; mp 44-46C. |
- 9
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[ 113602-62-3 ]

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[ 113589-14-3 ]
- 10
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[ 113602-62-3 ]

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[ 113602-69-0 ]