tert-Butyl diethylphosphonoacetate → HCID 67114131, compound
Reaction equation
[CH3:1][C:2](C)([O-])C.[Na+].C(OP([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(OCC)=O)C.O1CC1[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1>COCCOC>[C:19]([O:18][C:16]([CH:15]1[CH2:2][CH:1]1[C:27]1[CH:26]=[CH:31][CH:30]=[CH:29][N:28]=1)=[O:17])([CH3:20])([CH3:21])[CH3:22]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a stirred suspension of sodium tert-butoxide (7.63 g, 79.4 mmol) in 1,2-dimethoxyethane (70 mL) at ambient temperature was added tert-butyl diethylphosphonoacetate (20.0 g, 79.4 mmol) over 30 minutes, then allowed to stir a further 40 minutes then 3-(oxiran-2-yl)pyridine (4.8 g, 39.7 mmol) was added drop wise. The suspension was stirred at for 30 minutes then heated to 65° C. overnight. The reaction was poured onto ice and extracted with diethyl ether. The combined organic extracts were washed with saturated aqueous sodium chloride, dried (MgSO4), and evaporated to provide an orange oil which was purified by flash chromatography (elution solvent: 20% (v/v) hexane/dichloromethane) to obtain 3.0 g of purified material.
Workup
- stirringThe suspension was stirred at for 30 minutes
- additionThe reaction was poured onto ice
- extractionextracted with diethyl ether
- washThe combined organic extracts were washed with saturated aqueous sodium chloride
- dry with materialdried (MgSO4)
- customevaporated
- customto provide an orange oil which
- customwas purified by flash chromatography (elution solvent: 20% (v/v) hexane/dichloromethane)
Sources & evidence
- ORD record
- ord-6a27216bd44e4f9fa8c93bd18d7f244f
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426414B2
Reaction notes
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