Diethyl Carbonate → HCID 89894058, compound
Reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:14][NH2:15].C[O-].[Na+].[C:19](=[O:26])(OCC)OCC>CO>[NH2:14][N:15]1[CH2:12][C@H:10]([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[O:11][C:19]1=[O:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
(R)-2-(Benzyloxymethyl)oxirane (2.5 g, 15.23 mmol) was added dropwise to hydrazine mono-hydrate (4.67 g, 91 mmol), previously heated at 95° C., under vigorous stirring. The mixture was refluxed for 30 min. The excess of hydrazine hydrate was evaporated under vacuum for 3 h, at 53° C. and then at r.t., under vigorous magnetic stirring, for 18 h. A sticky colourless oil was obtained. The crude was dissolved in dry MeOH (5 mL) and a solution of sodium methoxide 0.5M in methanol (4.6 mL, 2.284 mmol), then diethyl carbonate (2.16 g, 18.27 mmol) were added dropwise. The mixture was refluxed for 6 h. The solvent was evaporated and the crude purified by flash silica-gel chromatography (DCM/MeOH=75:1) affording the title compound as a yellow oil that solidified on standing into a white solid (2.232 g, 10.04 mmol). Yield=66%.
Workup
- temperatureThe mixture was refluxed for 30 min
- customThe excess of hydrazine hydrate was evaporated under vacuum for 3 h, at 53° C.
- customA sticky colourless oil was obtained
- temperatureThe mixture was refluxed for 6 h
- customThe solvent was evaporated
- customthe crude purified by flash silica-gel chromatography (DCM/MeOH=75:1)
Sources & evidence
- ORD record
- ord-754d5b871db5404789aa4f9c16b59741
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09284306B2
Reaction notes
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