Reaction #4025321
Related Literature (1)
openreactiondata ↗doi:10.1039/C8SC04228D
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f232f282403a4eae975433a4a3521238No renderable structure data available
CC(C)COC(C)ONChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | O-[1-(2-methylpropoxy)ethyl]hydroxylamine |
|---|---|
| IUPAC Name | — |
| CAS Number | 860216-27-9 |
| Database ID | 9877377 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
O-[1-(2-methylpropoxy)ethyl]hydroxylamine (CAS 860216-27-9) 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 9877377
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-f232f282403a4eae975433a4a3521238Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-376c798cb5464815a94863dd5d5d8495Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Monomethyl suberate (25.0 g, 13.3 mmol, 1.0 eq) was dissolved in THF (300 mL) and DCM (300 mL). EDC.HCl (25.46 g, 13.3 mmol, 1.0 eq) was added to the stirred solution, followed by HOBt (17.95 g, 13.3 mmol, 1.0 eq) and triethylamine (48.5 mL, 34.5 mmol, 2.6 eq). O-(1-Isobutoxy-ethyl)-hydroxylamine (21.9 mL, 15.9 mmol, 1.2 eq) was added to the viscous solution and the reaction allowed to stir overnight at room temperature. The reaction mixture was concentrated under vacuum, DCM (350 mL) was added and washed with water (250 mL) and brine (200 mL). The organic layer was isolated, dried (MgSO4), filtered and concentrated in vacuo. The product was obtained as a white solid (36.6 g, 91% yield) LCMS purity 88%, m/z 302 (M++H)+. This was used in the next step without further purification. The reaction mixture was concentrated under vacuum, DCM (350 mL) was added washed with water (250 mL) and brine (200 mL) The organic layer was isolated dried (MgSO4) filtered concentrated in vacuo
Source ID: ord-8dd0d810010d46d8a4c80f1c4090e435Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Monomethyl suberate (25.0 g, 13.3 mmol, 1.0 eq) was dissolved in THF (300 mL) and DCM (300 mL). EDC.HCl (25.46 g, 13.3 mmol, 1.0 eq) was added to the stirred solution, followed by HOBt (17.95 g, 13.3 mmol, 1.0 eq) and triethylamine (48.5 mL, 34.5 mmol, 2.6 eq). O-(1-Isobutoxy-ethyl)-hydroxylamine (21.9 mL, 15.9 mmol, 1.2 eq) was added to the viscous solution and the reaction allowed to stir overnight at room temperature. The reaction mixture was concentrated under vacuum, DCM (350 mL) was added and washed with water (250 mL) and brine (200 mL). The organic layer was isolated, dried (MgSO4), filtered and concentrated in vacuo. The product was obtained as a white solid (36.6 g, 91% yield) LCMS purity 88%, m/z 302 (M++H)+. This was used in the next step without further purification. The reaction mixture was concentrated under vacuum, DCM (350 mL) was added washed with water (250 mL) and brine (200 mL) The organic layer was isolated dried (MgSO4) filtered concentrated in vacuo
Source ID: ord-8dd0d810010d46d8a4c80f1c4090e435Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f232f282403a4eae975433a4a3521238Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-376c798cb5464815a94863dd5d5d8495Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Monomethyl suberate (25.0 g, 13.3 mmol, 1.0 eq) was dissolved in THF (300 mL) and DCM (300 mL). EDC.HCl (25.46 g, 13.3 mmol, 1.0 eq) was added to the stirred solution, followed by HOBt (17.95 g, 13.3 mmol, 1.0 eq) and triethylamine (48.5 mL, 34.5 mmol, 2.6 eq). O-(1-Isobutoxy-ethyl)hydroxylamine (21.9 mL, 15.9 mmol, 1.2 eq) was added to the viscous solution and the reaction allowed to stir overnight at room temperature. The reaction mixture was concentrated under vacuum, DCM (350 mL) was added and washed with water (250 mL) and brine (200 mL). The organic layer was isolated, dried (MgSO4), filtered and concentrated in vacuo. The product was obtained as a white solid (36.6 g, 91% yield) LCMS purity 88%, m/z 302 (M++H)+. This was used in the next step without further purification. The reaction mixture was concentrated under vacuum, DCM (350 mL) was added washed with water (250 mL) and brine (200 mL) The organic layer was isolated dried (MgSO4) filtered concentrated in vacuo
Source ID: ord-f8fbab51b0e94b94a2000d9a033e727aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Monomethyl suberate (25.0 g, 13.3 mmol, 1.0 eq) was dissolved in THF (300 mL) and DCM (300 mL). EDC.HCl (25.46 g, 13.3 mmol, 1.0 eq) was added to the stirred solution, followed by HOBt (17.95 g, 13.3 mmol, 1.0 eq) and triethylamine (48.5 mL, 34.5 mmol, 2.6 eq). O-(1-Isobutoxy-ethyl)hydroxylamine (21.9 mL, 15.9 mmol, 1.2 eq) was added to the viscous solution and the reaction allowed to stir overnight at room temperature. The reaction mixture was concentrated under vacuum, DCM (350 mL) was added and washed with water (250 mL) and brine (200 mL). The organic layer was isolated, dried (MgSO4), filtered and concentrated in vacuo. The product was obtained as a white solid (36.6 g, 91% yield) LCMS purity 88%, m/z 302 (M++H)+. This was used in the next step without further purification. The reaction mixture was concentrated under vacuum, DCM (350 mL) was added washed with water (250 mL) and brine (200 mL) The organic layer was isolated dried (MgSO4) filtered concentrated in vacuo
Source ID: ord-f8fbab51b0e94b94a2000d9a033e727aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Monomethyl suberate (25.0 g, 13.3 mmol, 1.0 eq) was dissolved in THF (300 mL) and DCM (300 mL). EDC.HCl (25.46 g, 13.3 mmol, 1.0 eq) was added to the stirred solution, followed by HOBt (17.95 g, 13.3 mmol, 1.0 eq) and triethylamine (48.5 mL, 34.5 mmol, 2.6 eq). O-(1-Isobutoxy-ethyl)-hydroxylamine (21.9 mL, 15.9 mmol, 1.2 eq) was added to the viscous solution and the reaction allowed to stir overnight at room temperature. The reaction mixture was concentrated under vacuum, DCM (350 mL) was added and washed with water (250 mL) and brine (200 mL). The organic layer was isolated, dried (MgSO4), filtered and concentrated in vacuo. The product was obtained as a white solid (36.6 g, 91% yield) LCMS purity 88%, m/z 302 (M++H)+. This was used in the next step without further purification. The reaction mixture was concentrated under vacuum, DCM (350 mL) was added washed with water (250 mL) and brine (200 mL) The organic layer was isolated dried (MgSO4) filtered concentrated in vacuo
Source ID: ord-4569d4b02d824086a5e0d92da6a97dc4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Monomethyl suberate (25.0 g, 13.3 mmol, 1.0 eq) was dissolved in THF (300 mL) and DCM (300 mL). EDC.HCl (25.46 g, 13.3 mmol, 1.0 eq) was added to the stirred solution, followed by HOBt (17.95 g, 13.3 mmol, 1.0 eq) and triethylamine (48.5 mL, 34.5 mmol, 2.6 eq). O-(1-Isobutoxy-ethyl)-hydroxylamine (21.9 mL, 15.9 mmol, 1.2 eq) was added to the viscous solution and the reaction allowed to stir overnight at room temperature. The reaction mixture was concentrated under vacuum, DCM (350 mL) was added and washed with water (250 mL) and brine (200 mL). The organic layer was isolated, dried (MgSO4), filtered and concentrated in vacuo. The product was obtained as a white solid (36.6 g, 91% yield) LCMS purity 88%, m/z 302 (M++H)+. This was used in the next step without further purification. The reaction mixture was concentrated under vacuum, DCM (350 mL) was added washed with water (250 mL) and brine (200 mL) The organic layer was isolated dried (MgSO4) filtered concentrated in vacuo
Source ID: ord-4569d4b02d824086a5e0d92da6a97dc4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Monomethyl suberate (25.0 g, 13.3 mmol, 1.0 eq) was dissolved in THF (300 mL) and DCM (300 mL). EDC.HCl (25.46 g, 13.3 mmol, 1.0 eq) was added to the stirred solution, followed by HOBt (17.95 g, 13.3 mmol, 1.0 eq) and triethylamine (48.5 mL, 34.5 mmol, 2.6 eq). O-(1-Isobutoxy-ethyl)-hydroxylamine (21.9 mL, 15.9 mmol, 1.2 eq) was added to the viscous solution and the reaction allowed to stir overnight at room temperature. The reaction mixture was concentrated under vacuum, DCM (350 mL) was added and washed with water (250 mL) and brine (200 mL). The organic layer was isolated, dried (MgSO4), filtered and concentrated in vacuo. The product was obtained as a white solid (36.6 g, 91% yield) LCMS purity 88%, m/z 302 (M++H)+. This was used in the next step without further purification. The reaction mixture was concentrated under vacuum, DCM (350 mL) was added washed with water (250 mL) and brine (200 mL) The organic layer was isolated dried (MgSO4) filtered concentrated in vacuo
Source ID: ord-8dd0d810010d46d8a4c80f1c4090e435Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f232f282403a4eae975433a4a3521238PubChem References
These sources are listed in the compound's public database record.
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